Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity

Save this PDF as:
Size: px
Start display at page:

Download "Synthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity"

Transcription

1 Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Insitute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, China.

2 Table of Contents 1. General Experimental Procedure... S2 2. Full Synthetic Sequence to Glaucogenin D from hirundigenin-type intermediate 6... S3 3. Experimental Section... S3 4. Comparison of 1 H- and 13 CNMR Data for Natural vs Synthetic Glaucogenin D... S15 5. NMR Spectra... S16 S1

3 1. General Experimental Procedure: All reactions utilizing air- or moisture-sensitive reagents were carried out in flame-dried glassware under an argon atmosphere, unless otherwise stated. CH 2 Cl 2, DMF, t BuOH and THF were distilled prior to use according to the standard protocols. Other reagents were purchased and used as received without further purification unless otherwise stated. Reactions were magnetically stirred and monitored by thin layer chromatography (TLC) with mm pre-coated silica gel (10-40 μm) plates. Compounds were visualized with UV light and/or by staining with ethanolic phosphomolybdic acid (PMA) followed by heating on a hot plate. Flash chromatography was performed with silica gel ( mesh) under pressure. Yields refer to chromatographically and spectroscopically ( 1 H NMR) homogeneous compounds, unless otherwise stated. NMR spectra were recorded on Varian-300, Bruker-400 and Bruker-500 spectrometers in CDCl 3 with TMS as the internal standard, unless otherwise stated. Chemical shifts (δ) are given in ppm relative to residual chloroform (δ 7.26 for 1 H NMR and 77.2 for 13 C NMR), coupling constants (J) in Hz. Multiplicity is indicated as follows: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; br, broad. IR spectra were collected on Avatar 330 FT-IR spectrometer. Melting points were determined on SGW X-4 microscopic melting point apparatus and were uncorrected. Optical rotations were determined on JASCO P-1030 Polarimeter in the solvent indicated. High-resolution mass spectra were recorded on IonSpec 4.7 Tesla FTMS or Bruker Daltonics, Inc. APEXIII 7.0 TESLA FTMS. S2

4 3. Full Synthetic Sequence to Glaucogenin D from Hirundigenin-type Intermediate 6: 4. Experimental Section: A solution of 7 (15 mg, mmol) and tetraphenylporphyrin (TPP) (ca. 1 mg) in dry DCM (5 ml) was irradiated with an incandescent lamp (200 W) while oxygen was being passed through the solution. The mixture was stirred at 0 o C for 1 h. Evaporation of the solvent under reduced pressure and flash chromatography of the residue (EtOAc: PE=1:3) afforded 9 (16 mg, >99%) as a white solid. [α] 26 D 10.9 (c 0.65, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 3419, 2931, 2857, 1748, 1428, 1384, 1104, 702, 508; 1 H NMR (300 MHz, CDCl 3 ): 0.73 (s, 3H), 1.04 (s, 9H), 1.61 (s, 3H), 2.06 (s, 3H), 2.89 (d, J = 6.6 Hz, 1H), 3.49 (d, J = 9.3 Hz, 1H), 3.56 (m, 1H), 3.77 (d, J = 9.3 Hz, 1H), 4.65 (d, J = 6.9 Hz, 1H), 5.89 (m, 1H), 6.33 (s, 3H), S3

5 (m, 6H), 7.61 (s, 1H), 7.66 (br d, J = 6.9 Hz, 4H); 13 C NMR (100 MHz, CDCl 3 ) δ 169.7, 136.0, 135.0, 134.9, 131.2, 129.7, 127.7, 124.7, 120.0, 113.3, 99.1, 87.4, 72.6, 72.4, 60.4, 59.0, 45.8, 40.0, 38.1, 37.2, 34.6, 31.7, 29.2, 27.3, 25.9, 25.6, 21.5, 21.4, 19.4, 13.2; HRMS (ESI) m/z (M+Na) + calcd for C 39 H 50 O 8 SiNa , obsd A solution of 7 (128 mg, 0.2 mmol) and tetraphenylporphyrin (TPP) (ca. 1 mg) in dry DCM (20 ml) was irradiated with an incandescent lamp (200 W) while oxygen was being passed through the solution. After the mixture was stirred at 0 o C for 1 h, the solvent was removed in vacuo. To another solution of FeSO 4 7H 2 O (115 mg, 0.4 mmol) and I 2 (106 mg, 0.4 mmol) in 2 ml MeOH was added under argon a solution of above mixtures in MeOH (6 ml). After stirred at RT for 1 h, the reaction mixture was quenched with saturated Na 2 S 2 O 3 solution (15 ml) and extracted with DCM (3 20 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. To the crude residue was added DCM (2 ml), DBU (0.3 ml, 2 mmol) and the mixture was stirred at 60 o C for 2 h. After the reaction mixture was cooled to RT, 5% HCl (10 ml) was added and the water phase was extracted with DCM (3 20 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc: PE=1:10) to afford 11 (109 mg, 83% over 3 steps) as a white solid. [α] 25 D 31.8 (c 1.60, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 2931, 2857, 1764, 1729, 1427, 1110, 702, 508; 1 H NMR (400 MHz, CDCl 3 ): 0.73 (s, 3H), 1.08 (s, 9H), 1.66 (s, 3H), 2.15(s, 3H), 2.58 (m, 1H), 3.58 (d, J = 8.0 Hz, 1H), 3.60 (m, 1H), 5.48 (dd, J = 8.0, 4.4 Hz, 1H), 6.00 (m, 1H), 6.19 (s, 1H), 6.32 (d, J = 4.4 Hz, 1H), (m, 6H), 7.70 (m, 4H); 13 C NMR (101 MHz, CDCl 3 ) δ 170.8, 169.6, 142.1, 135.8, 134.7, 134.0, 130.1, 129.5, 127.5, 117.3, 115.2, 97.9, 79.8, 72.0, 54. 8, 51.3, S4

6 39.3, 37. 9, 36.1, 34.8, 31.8, 29.6, 27.5, 27.0, 25.0, 22.9, 21.1, 19.1, 11.4; HRMS (ESI) m/z (M+Na) + calcd for C 39 H 48 O 7 SiNa , obsd A solution of 7 (99 mg, 0.15 mmol) and tetraphenylporphyrin (TPP) (ca. 1 mg) in dry DCM (10 ml) was irradiated with an incandescent lamp (200 W) and oxygen was passed through the solution. After the mixture was stirred at 0 o C for 1 h, the solvent was removed in vacuo. To another solution of FeSO 4 7H 2 O (83 mg, 0.3 mmol) and TEMPO (47 mg, 0.3 mmol) in 1 ml MeOH was added under argon a solution of above mixture in MeOH (3 ml). After stirred at RT for 1 h, the reaction mixture was quenched with 5% HCl solution (10 ml) and extracted with DCM (3 20 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc: PE=1:10) to afford 13 (87 mg, 71% over 2 steps) as a white solid. [α] 23 D 10.3 (c 1.65, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 2932, 2856, 1759, 1728, 1375, 1108, 702, 507; 1 H NMR (400 MHz, CDCl 3 ): 0.70 (s, 3H), 0.94 (s, 3H), 0.98 (s, 3H), 1.05 (s, 9H), 1.09 (s, 6H), 1.68 (s, 3H), 2.09 (s, 3H), 2.98 (d, J = 8.8 Hz, 1H), 3.16 (m, 1H), 3.57 (m, 1H), 4.08 (d, J = 6.0 Hz, 1H), 4.12 (d, J = 6.0 Hz, 1H), 5.67 (d, J = 7.2 Hz, 1H), 6.22 (m, 1H), 6.26 (s, 1H), (m, 6H), 7.67 (m, 4H); 13 C NMR (101 MHz, CDCl 3 ) δ 170.4, 169.2, 135.7, 134.7, 134.6, 134.5, 133.3, 129.5, 127.5, 119.5, 100.9, 92.9, 77.7, 75.5, 72.0, 60.3, 59.5, 59.3, 49.7, 40.6, 40.5, 39.4, 37.8, 36.0, 34.8, 34.2, 33.8, 31.8, 29.9, 27.0, 26.7, 26.2, 21.1, 20.9, 20.8, 19.1, 16.9, 11.4; HRMS (ESI) m/z (M+Na) + calcd for C 48 H 67 NO 8 SiNa , obsd S5

7 To a solution of 12 (15 mg, 0.02 mmol) and dibenzo-18-crown-6 (18 mg, 0.05 mmol) in dry DCM (1 ml) was added KMnO 4 (6.3 mg, 0.04 mmol) at 0 o C. After stirred at this temperature for 2 h, the reaction mixture was warmed to RT and stirring was continued for another 3.5 h. Then the reaction mixture was quenched successively with saturated NaHSO 3 solution, 5% HCl solution and extracted with DCM (3 10 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc: PE=1:10 1:2) to afford 15 (11 mg, 70%, 75% brsm) as a white solid, together with unreacted starting material (1 mg, 7%). [α] 26 D 37.5 (c 0.85, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 3493, 2932, 2857, 1732, 1214, 1109, 702, 506; 1 H NMR (400 MHz, CDCl 3 ): 0.79 (s, 3H), 0.97 (s, 1H), 0.98 (s, 1H), 1.05 (s, 9H), 1.09 (s, 3H), 1.10 (s, 3H), 1.65 (s, 3H), 2.83 (m, 1H), 2.93 (d, J = 9.6 Hz, 1H), 3.59 (m, 1H), 3.85 (s, 1H), 3.93 (t, J = 8.8 Hz, 1H), 4.10 (m, 2H), 4.19 (dd, J = 9.6, 8.0 Hz, 1H), 4.24 (d, J = 10.0 Hz, 1H), 5.65 (q, J = 8.8 Hz, 1H), (m, 6H), 7.66 (m, 4H); 13 C NMR (101 MHz, CDCl 3 ) δ 175.9, 135.7, 134.8, 134.6, 129.5, 127.5, 116.9, 93.2, 80.0, 77.2, 73.9, 71.9, 69.2, 67.9, 59.7, 59.4, 58.5, 57.9, 40.8, 40.7, 39.4, 38.1, 36.6, 35.1, 34.9, 34.3, 34.1, 31.1, 27.0, 24.5, 24.2, 21.7, 21.3, 21.1, 19.1, 16.9, 14.4; HRMS (ESI) m/z (M+H) + calcd for C 46 H 68 NO 8 Si , obsd To a solution of 15 (18 mg, mmol) in dry DMF (1 ml) was added PDC (87 mg, 0.23 mmol) at RT. After stirred at RT for 28 h, the reaction mixture was quenched with water and extracted with DCM (3 10 ml). The combined organic layers were washed with water (3 10 ml), brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc: PE=1:5) to afford 16 (15 mg, 83%) as a white solid. [α] 22 D 36.7 (c 1.75, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 3479, 2932, 2856, 1732, 1249, 1111, 702, 501; 1 H NMR (400 MHz, CDCl 3 ): 0.71 (s, 3H), 0.96 (s, 1H), 0.98 (s, 1H), 1.06 (s, 9H), 1.08 (s, 3H), 1.10 (s, S6

8 3H), 1.64 (s, 3H), 2.26 (m, 1H), 2.64 (dd, J = 18.4, 7.2 Hz, 1H), 2.81 (m, 1H), 2.92 (d, J = 10.0 Hz, 1H), 3.63 (m, 1H), 3.92 (t, J = 9.2 Hz, 1H), 4.05 (d, J = 10.0 Hz, 1H), 4.08 (s, 1H), 4.23(m, 2H), 5.74 (q, J = 8.8 Hz, 1H), (m, 6H), 7.66 (m, 4H); 13 C NMR (101 MHz, CDCl 3 ) δ 204.6, 172.7, 135.7, 134.6, 134.4, 129.6, 127.6, 116.9, 93.2, 80.2, 77.2, 74.1, 71.6, 69.1, 60.9, 59.8, 59.5, 57.5, 40.8, 40.7, 40.1, 37.8, 36.3, 35.3, 34.4, 34.1, 31.3, 27.0, 24.5, 23.8, 21.4, 21.2, 21.0, 19.1, 16.9, 13.3; HRMS (ESI) m/z (M+Na) + calcd for C 46 H 65 NO 8 SiH , obsd To a solution of i Pr 2 NH (0.26 ml, 1.83 mmol) in 1 ml anhydrous THF was added at 0 o C a solution of 2.5 M n-buli (in hexane) (0.78 ml, 1.83 mmol). After stirred at this temperature for 30 min, the mixture was cooled to -78 o C and a solution of 16 (70 mg, mmol) in 1.5 ml THF and 0.2 ml HMPA was added. After 1 h, TMSCl (0.23 ml,1.80 mmol)was added and stirring was continued for 30 min. Then the mixture was warmed to 0 o C and stirred for another 1 h before being quenched with saturated NaHCO 3 solution and extracted with EtOAc (3 20 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue of silyl enol ether 17 was used in the next step without further purification. 1 H NMR (400 MHz, CDCl 3 ): 0.05 (s, 9H), 0.14 (s, 9H), 0.70 (s, 3H), 1.01 (s, 3H), 1.07 (s, 9H), 1.09 (s, 3H), 1.63 (s, 3H), (m, 1H), 3.08 (d, J = 10.0 Hz, 1H), (m, 1H), 3.89 (t, J = 9.6 Hz, 1H), 4.06 (d, J = 10.0 Hz, 1H), 4.12 (t, J = 8.0 Hz, 1H), 4.22 (d, J = 10.0 Hz, 1H), 4.51 (d, J = 2.8 Hz, 1H), 5.36 (dt, J = 8.0, 10.0 Hz, 1H), (m, 6H), 7.68 (m, 4H); HRMS (ESI) m/z (M+H) + calcd for C 52 H 82 NO 8 Si , obsd S7

9 Condition A: To the crude mixture of 17 (prepared from 16 (70 mg, mmol) as described above) in 2 ml anhydrous THF was added NBS (95 mg, mmol) at RT. After stirred at this temperature for 3 h, the reaction mixture was quenched with saturated NaHCO 3 solution, and extracted with DCM (3 30 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc: PE=1:15 1:10) to afford 18 (90 mg, >99%) as a white solid. Condition B: To the crude mixture of 17 (prepared from 16 (7 mg, mmol) as described above) in 1 ml anhydrous THF was added PhSeBr (21 mg, mmol) at RT. After stirred at this temperature for 11 h, the reaction mixture was quenched with saturated NaHCO 3 solution, and extracted with DCM (3 10 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc: PE=1:15 1:10) to afford 18 (10 mg, >99%) as a white solid. Compound 18: [α] 28 D 23.7 (c 1.40, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 2930, 2856, 1744, 1730, 1471, 1252, 1111, 702, 503; 1 H NMR (300 MHz, CDCl 3 ): 0.15 (s, 9H), 0.68 (s, 3H), 1.00 (s, 6H), 1.08 (s, 9H), 1.09 (s, 3H), 1.10 (s, 3H), 1.64 (s, 3H), 2.19 (m, 1H), (m, 1H), (m, 1H), 2.92 (d, J = 10.0 Hz, 1H), (m, 1H), 3.72 (d, J = 11.6 Hz, 1H), 3.86 (t, J = 9.2 Hz, 1H), 4.01 (d, J = 10.4 Hz, 1H), (m, 2H), 5.68 (q, J = 9.2 Hz, 1H), (m, 6H), 7.68 (m, 4H); 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , 83.94, 73.48, 71.78, 69.28, 62.56, 60.20, 59.88, 57.46, 47.73, 44.07, 41.02, 40.91, 39.10, 36.75, 35.48, 34.98, 34.28, 31.37, 29.87, 27.17, 24.74, 22.13, 21.36, 21.23, 19.27, 17.05, 13.99, 2.73; HRMS (ESI) m/z (M+Na) + calcd for C 49 H 72 BrNO 8 Si 2 Na , obsd S8

10 To the crude mixture of 17 (prepared from 16 (157 mg, 0.2 mmol) as described above) in 5 ml anhydrous DCM was added PhSeCl (384 mg, 2 mmol) at RT. After stirred at this temperature for 2.5 h, the reaction mixture was quenched with saturated NaHCO 3 solution, and extracted with DCM (3 30 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc: PE=1:8) to afford 20 (201 mg, 99%) as a white solid. [α] 27 D 26.4 (c 2.50, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 2932, 2857, 1747,1723, 1250, 1111, 847, 702, 509; 1 H NMR (400 MHz, CDCl 3 ): 0.21 (s, 9H), 0.64 (s, 3H), 0.98 (s, 3H), 0.99 (s, 3H), 1.07 (s, 9H), 1.09 (s, 3H), 1.10 (s, 3H), 1.64 (s, 3H), (m, 1H), 2.48 (m, 1H), (m, 3H), (m, 1H), 3.87 (t, J = 9.2 Hz, 1H), 4.03 (d, J = 10.0 Hz, 1H), (m, 2H), 5.73 (q, J = 9.2 Hz, 1H), (m, 3H), (m, 6H), (m, 2H), (m, 4H); 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , 93.45, 84.04, 77.29, 73.21, 72.28, 69.29, 62.77, 59.97, 59.62, 57.47, 51.25, 43.61, 41.11, 40.97, 38.95, 36.64, 35.55, 35.07, 34.40, 31.45, 29.87, 27.18, 24.76, 23.60, 22.16, 21.43, 21.25, 19.29, 17.09, 13.54, 3.20; LR-MS (ESI) m/z (M+Na) + : (Acquisition of HRMS data (ESI or MALDI) was met with failure possiblely due to the high MW of the molecule). To a solution of 20 (61 mg, 0.06 mmol) in 3 ml CH 3 CN was added an aqueous 40% HF solution (0.03 ml, 0.6 mmol) and the resulting solution was stirred at RT for 1 day. S9

11 Then the reaction mixture was quenched with saturated NaHCO 3 solution (15 ml) and extracted with EtOAc (3 20 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue of 21 was dissolved in DCM (10 ml) and O 3 was passed through the solution while cooling at 78 o C. After 1 min, a blue color appeared and the ozone bubbler was replaced with an argon bubbler to give a colorless solution. Then 0.01 ml i Pr 2 NH was added and the solution was warmed to RT. To the crude mixture, obtained by evaporation of the solvent under reduced pressure, in 2 ml toluene was added 0.01 ml i Pr 2 NH and the resulting solution was stirred at 60 o C for 1 h. Evaporation of the solvent under reduced pressure and flash chromatography of the residue (EtOAc: PE=1:1 2:1) afforded 22 (17 mg, 52%) as a white solid. Compound 21: [α] 27 D 61.7 (c 1.00, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 3536, 3311, 2934, 2870, 1745, 1706, 1270, 738; 1 H NMR (400 MHz, CDCl 3 ): 0.72 (s, 3H), 1.01 (s, 3H), 1.02 (s, 3H), 1.10 (s, 3H), 1.12 (s,3h), 1.65 (s, 3H), 2.40 (m, 1H), 2.63 (m, 1H), 2.92 (m, 2H), 3.00 (d, J = 11.2 Hz, 1H), 3.69 (m, 1H), 3.94 (t, J = 9.2 Hz, 1H), 4.07 (m, 2H), 4.24 (m, 2H), 5.82 (q, J = 8.4 Hz, 1H), 7.28 (m, 3H), 7.65 (m, 2H); 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , , 93.46, 81.11, 74.15, 70.30, 69.46, 61.26, 60.12, 59.82, 57.83, 50.70, 44.15, 40.98, 40.88, 38.31, 36.40, 35.54, 34.52, 34.25, 31.18, 24.59, 24.29, 21.67, 21.39, 21.22, 17.07, 13.38; HRMS (ESI) m/z (M+Na) + calcd for C 36 H 51 NO 8 SeNa , obsd Compound 22: [α] 26 D 71.4 (c 0.85, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 3467, 2933, 1739, 1674, 1466, 1239, 1061, 877; 1 H NMR (400 MHz, CDCl 3 ): 0.99 (s, 3H), 1.00 (s, 3H), 1.11 (s, 6H), 1.31 (s, 3H), 1.61 (s, 3H), 2.55 (m, 2H), 2.64 (m, 1H), 2.85 (d, J = 9.2 Hz, 1H), 3.35 (m, 1H), 3.73 (m, 1H), 3.95 (s, 1H), 4.00 (m, 2H), 4.15 (m, 2H), 5.89 (s, 1H), 5.90 (m, 1H); 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , 79.73, 74.77, 73.18, 70.48, 60.24, 59.82, 59.59, 53.44, 43.14, 40.97, 40.83, 40.22, 38.25, 34.27, 34.13, 31.81, 27.00, 24.23, 24.10, 21.53, 21.19, 20.75, 17.09; HRMS (ESI) m/z (M+Na) + calcd for C 30 H 45 NO 8 Na , obsd S10

12 Preparation of then SmI 2 solution in THF: To a suspension of powdered Sm (105 mg, mmol) in 2 ml THF was added CH 2 I 2 (27 μl, mmol). The mixture was stirred at room temperature for 1 h, observing the appearance of a dark blue color. To a solution of 22 (16 mg,0.029 mmol) in THF (1 ml) and t-buoh (0.1 ml) was added at -78 o C a solution of SmI 2 in THF (1 ml, ca mmol) freshly prepared as described above. The reaction mixture was stirred at this temperature for 10 min and opened to air untill a yellow color appeared. Then a saturated NaHCO 3 solution (15 ml) was added, and the mixture was warmed to RT and extracted with DCM (3 15 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. To this crude mixture in 2 ml MeOH at 0 o C was added sequentially CeCl 3 7H 2 O (32 mg, mmol), NaBH 4 (4 mg, mmol). After stirred at 0 o C for 1 h, the reaction mixture was quenched with saturated NH 4 Cl solution (15 ml) and extracted with DCM (3 15 ml). The combined organic layers were washed with brine, dried over Na 2 SO 4, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc: PE=1:1 2:1) to afford 23 (9 mg, 58% for 2 steps) as a white solid. [α] 27 D -3.5 (c 0.65, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 3432, 2930, 2854, 1736, 1464, 1163, 1048, 828; 1 H NMR (400 MHz, CDCl 3 ): 1.01 (s, 3H), 1.13 (s, 3H), 1.14 (s, 3H), 1.26 (s, 6H), 1.65 (s, 3H), (m, 1H), (m, 2H), 2.82 (d, J = 9.2 Hz, 1H), (m, 1H), (m, 1H), 3.99 (dd, J = 10.0, 5.6 Hz, 1H), 4.11 (dd, J = 9.6, 6.8 Hz, 1H), 4.17 (d, J = 9.6 Hz, 1H), 4.24 (d, J = 9.6 Hz, 1H), 4.64 (br d, J = 9.6 Hz, 1H), 5.41 (s, 1H), 5.86 (dt, J = 9.6, 6.4 Hz, 1H); 13 C NMR (101 MHz, CDCl 3 ) δ , , , , 93.20, 77.11, 72.36, 71.57, 70.48, 68.20, 60.07, 59.69, 59.36, 49.21, 48.30, 41.67, 40.96, 40.87, 38.83, 36.23, S11

13 34.24, 34.21, 31.37, 24.88, 24.29, 22.72, 21.63, 21.31, 18.03, 17.13; HRMS (ESI) m/z (M+H) + calcd for C 30 H 48 NO , obsd To a solution of 23 (10 mg, mmol) in 2 ml toluene was added 0.01 ml i Pr 2 NH and the resulting solution was stirred at 120 o C for 1 h. Evaporation of the solvent under reduced pressure and flash chromatography of the residue (EtOAc: PE=1:1 EA) afforded 24 (6 mg, 85%) as a white solid. [α] 28 D 2.6 (c 0.30, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 3416, 2930, 2854, 1725, 1151, 1047, 809; 1 H NMR (400 MHz, CDCl 3 ): 1.09 (s, 3H), 1.55 (s, 3H), 3.22 (d, J = 8.0 Hz, 1H), (m, 1H), 4.10 (dd, J = 6.4, 4.0 Hz, 1H), 4.22 (dd, J = 10.4, 6.4 Hz, 1H), 4.39 (d, J = 12.8 Hz, 1H), (m, 2H), 5.05 (dd, J = 12.4, 1.2 Hz, 1H), 5.39 (s, 1H), (m, 1H); 13 C NMR (101 MHz, CDCl 3 ) δ , , , , , , 78.31, 71.49, 71.21, 71.11, 70.25, 56.60, 50.67, 50.60, 41.73, 38.18, 37.10, 31.63, 29.36, 23.21, 19.94; HRMS (ESI) m/z (M+Na) + calcd for C 21 H 28 O 6 Na , obsd To a solution of 24 (3 mg, mmol) in 1 ml n PrOH was added RhCl(PPh 3 ) 3 1 mg and the resulting solution was stirred at 120 o C for 2 h. Evaporation of the solvent under reduced pressure and flash chromatography of the residue (EtOAc: PE=2:1) afforded glaucogenin D, 4 (2 mg, 66%) as a white solid. [α] 29 D 73.6 (c 0.09, CHCl 3 ); m.p ; IR (KBr, cm -1 ) 3425, 2929, 2855, 1737, 1383, 1083, 807, 609; 1 H NMR (400 MHz, CDCl 3 ): 0.99 (s, 3H), 1.54 (s, 3H), (m, 1H), 3.45 (d, J = 1 Since we can not obtain a crystal form of glaucogenin D, the m.p. data herein is much smaller than the reported data (m.p o C, white needle crystal from acetone-h 2 O). See: Dou, J.; Bi, Z.-M.; Zhang, Y.-Q.; Li, P. Chin. J. Nat. Med. 2006, 4, 192. S12

14 7.6 Hz, 1H), (m, 1H), 3.85 (t, J = 9.2 Hz, 1H), 4.17 (t, J = 8.8 Hz, 1H), 4.62 (br d, J = 10.0 Hz, 1H), (m, 1 H), 5.39 (s, 1H), 6.26 (s, 1H); 1 H NMR (400 MHz, Py): 0.91 (s, 3H), 1.51 (s, 3H), 3.59 (d, J = 8.0 Hz, 1H), 3.84 (m, 1H), 3.91 (dd, J = 9.6, 8.8 Hz, 1H), 4.11 (dd, J = 8.4, 7.2 Hz, 1H), 5.07 (d, J = 9.6 Hz, 1H), 5.43 (dt, J = 9.2, 7.6 Hz, 1H), 5.75 (s, 1H), 6.46 (s, 1H); 13 C NMR (101 MHz, Py) δ , , , , , , 75.84, 71.09, 67.97, 67.87, 56.39, 51.40, 50.81, 42.81, 38.79, 36.58, 32.40, 30.22, 24.80, 23.73, 17.92; HRMS (ESI) m/z (M-H) - calcd for C 21 H 27 O , obsd To a solution of 12 (8 mg, 0.01 mmol) in 1 ml toluene was added 0.01 ml i Pr 2 NH and the resulting solution was stirred at 120 o C for 2 h. Evaporation of the solvent under reduced pressure and flash chromatography of the residue (EtOAc: PE=1:15 1:5) afforded 25 (6 mg, 95%) as a white solid. [α] 24 D 2.7 (c 0.85, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 2930, 2856, 1715, 1427, 1230, 1109, 702, 508; 1 H NMR (400 MHz, CDCl 3 ): 0.84 (s, 3H), 1.05 (s, 9H), 1.51 (s, 3H), 2.33 (m, 1H), 2.51 (m, 1H), 3.16 (d, J = 7.6 Hz, 1H), (m, 1H), 4.10 (dd, J = 10.8, 4.0 Hz, 1H), 4.19 (dd, J = 10.8, 6.0 Hz, 1H), 4.31 (d, J = 12.4 Hz, 1H), 4.42 (d, J = 12.4 Hz, 1H), 5.18 (m, 1H), 5.59 (m, 1H), 5.89 (m, 1H), (m, 6H), 7.66 (m, 4H); 13 C NMR (101 MHz, CDCl 3 ) δ 173.4, 142.0, 136.4, 135.7, 134.7, 134.6, 129.5, 127.9, 127.5, 126.6, 115.6, 79.9, 72.0, 70.8, 70.3, 56.9, 51.3, 40.3, 37.7, 37.2, 34. 8, 31.3, 28.8, 28.7, 27.0, 23.0, 19.1, 14.0; HRMS (ESI) m/z (M+Na) + calcd for C 37 H 46 O 5 SiNa , obsd S13

15 Condition A: To a solution of 25 (14 mg, mmol) in 1 ml anhydrous toluene was added 0.01 ml DIPEA and RuCl 2 (PPh 3 ) 2 (19 mg, 0.02 mmol) and the resulting solution was stirred at 120 o C for 24 h. Evaporation of the solvent under reduced pressure and flash chromatography of the residue (EtOAc: PE=1:10) afforded 10 (10 mg, 71%, >99% brsm) as a white solid, together with unreacted starting material (4 mg, 39%). Condition B: To a solution of 25 (5 mg, mmol) in 1 ml n PrOH was added RhCl(PPh 3 ) 3 (1 mg, mmol) and the resulting solution was stirred at 110 o C for 1.5 h. Evaporation of the solvent under reduced pressure and flash chromatography of the residue (EtOAc: PE=1:10) afforded 10 (5mg, >99%) as a white solid. Compound 10: [α] 26 D 27.9 (c 1.75, CHCl 3 ); mp o C; IR (KBr, cm -1 ) 2931, 2856, 1723, 1654, 1110, 865; 1 H NMR (400 MHz, CDCl 3 ): 0.68 (s, 3H), 1.05 (s, 9H), 1.26 (s, 3H), 2.06 (m, 1H), 2.56 (m, 1H), 3.42 (d, J = 7.6 Hz, 1H), (m, 1H), 3.79 (t, J = 9.2 Hz, 1H), 4.21 (t, J = 7.6 Hz, 1H), 5.36 (dt, J = 9.2, 7.6 Hz, 1H), 6.00 (br s, 1H), 6.25(s, 1H), (m, 6H), 7.67 (br d, J = 7.2 Hz, 4H); 13 C NMR (101 MHz, CDCl 3 ) δ 170.7, 143.2, 135.7, 134.7, 134.6, 130.1, 129.5, 127.5, 117.1, 113.8, 75.1, 72.0, 67.7, 55.4, 51.8, 39.3, 37.9, 36.1, 34.8, 31.8, 29.6, 28.4, 27.0, 24.6, 23.8, 19.1, 11.4; HRMS (MALDI) m/z (M+Na) + calcd for C 37 H 46 O 5 SiNa , obsd S14

16 5. Comparison of 1 H- and 13 CNMR Data for Natural vs Synthetic Glaucogenin D. Comparison of 1 H NMR chemical shifts (Py-d5) Proton Natural Glaucogenin D 2 Synthetic Glaucogenin D (400 MHz) Δδ 18-CH 6.46 (s) 6.46 (s) 0 6-CH 5.75 (d, J = 1.5 Hz) 5.75 (s) 0 16-CH 5.43 (dd, J = 9.0, 7.8 Hz) 5.43 (dt, J = 9.2, 7.6 Hz) 0 7-CH 5.06 (d, J = 9.5 Hz) 5.07 (d, J = 9.6 Hz) CH α 4.11 (dd, J = 8.5, 7.0 Hz) 4.11 (dd, J = 8.4, 7.2 Hz) 0 15-CH β 3.91 (t, J = 9.3 Hz) 3.91 (dd, J = 9.6, 8.8 Hz) 0 3-CH 3.84 (m) 3.84 (m) 0 17-CH 3.59 (d, J = 9.0 Hz) 3.59 (d, J = 8.0 Hz) 0 21-Me 1.51 (s) 1.51 (s) 0 19-Me 0.92 (s) 0.91 (s) 0.01 Comparison of 13 C NMR chemical shifts (Py-d5) Synthetic Glaucogenin D Proton Natural Glaucogenin D 2 (100 MHz) Δδ C C C C C C C C C C C C C C C C C C C C C Dou, J.; Bi, Z.-M.; Zhang, Y.-Q.; Li, P. Chin. J. Nat. Med. 2006, 4, 192. S15

17 5. NMR Spectra: S16

18 1 H NMR (after exchange with D 2 O) 1 H NMR (original spectrum) S17

19 S18

20 COSY S19

21 NOESY S20

22 NOESY S21

23 S22

24 S23

25 DEPT 135 DEPT C NMR S24

26 S25

27 S26

28 S27

29 S28

30 DEPT 135 DEPT C NMR S29

31 S30

32 S31

33 S32

34 S33

35 S34

36 S35

37 DEPT 135 DEPT C NMR S36

38 S37

39 1 H NMR (after exchange with D 2 O) 1 H NMR (original spectrum) S38

40 S39

41 DEPT 135 DEPT C NMR S40

42 S41

43 S42

44 1 H NMR (after exchange with D 2 O) 1 H NMR (original spectrum) S43

45 S44

46 DEPT 135 DEPT C NMR S45

47 S46

48 S47

49 S48

50 DEPT 135 DEPT C NMR S49

51 S50

52 S51

53 DEPT 135 DEPT C NMR S52

54 S53

55 S54

56 DEPT 135 DEPT C NMR S55

57 S56

58 S57

59 S58

60 DEPT 135 DEPT C NMR S59

61 S60

62 S61

63 DEPT 135 DEPT C NMR S62

64 S63

65 grease S64

66 DEPT 135 DEPT 90 grease 13 C NMR S65

67 S66

68 S67

69 Glaucogenin D (100 MHz, Py-d5) S68

Supporting Information

Supporting Information Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,

More information

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C

The First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,

More information

SYNTHESIS OF A 3-THIOMANNOSIDE

SYNTHESIS OF A 3-THIOMANNOSIDE Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,

More information

Supporting Information

Supporting Information Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,

More information

Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain

Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry

More information

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12

Supporting Information. Table of Contents. 1. General Notes Experimental Details 3-12 Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents

More information

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes

Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic

More information

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon

Tetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone

More information

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes

Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi

More information

Supporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones

Supporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Supporting Information Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Marco Bandini,* Riccardo Sinisi, Achille Umani-Ronchi* Dipartimento di Chimica Organica G. Ciamician, Università

More information

Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts

Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site of Acid Catalysts Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Divergent Synthesis of CF 3 -Substituted Polycyclic Skeletons Based on Control of Activation Site

More information

Supporting Information

Supporting Information Supporting Information Divergent Reactivity of gem-difluoro-enolates towards Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of -Ketoamides Mallu Kesava Reddy, Isai Ramakrishna,

More information

Supporting Information

Supporting Information Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a

More information

Indium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols

Indium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols Supporting Information Indium Triflate-Assisted ucleophilic Aromatic Substitution Reactions of itrosobezene-derived Cycloadducts with Alcohols Baiyuan Yang and Marvin J. Miller* Department of Chemistry

More information

hydroxyanthraquinones related to proisocrinins

hydroxyanthraquinones related to proisocrinins Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some

More information

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis

Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,

More information

Supplementary Table S1: Response evaluation of FDA- approved drugs

Supplementary Table S1: Response evaluation of FDA- approved drugs SUPPLEMENTARY DATA, FIGURES AND TABLE BIOLOGICAL DATA Spheroids MARY-X size distribution, morphology and drug screening data Supplementary Figure S1: Spheroids MARY-X size distribution. Spheroid size was

More information

Supporting Information

Supporting Information Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and

More information

Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis

Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School

More information

Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801.

Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Fast and Flexible Synthesis of Pantothenic Acid and CJ-15,801. Alan L. Sewell a, Mathew V. J. Villa a, Mhairi Matheson a, William G. Whittingham b, Rodolfo Marquez a*. a) WestCHEM, School of Chemistry,

More information

Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle

Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl

More information

Supporting Information for. A New Method for the Cleavage of Nitrobenzyl Amides and Ethers

Supporting Information for. A New Method for the Cleavage of Nitrobenzyl Amides and Ethers SI- 1 Supporting Information for A ew Method for the Cleavage of itrobenzyl Amides and Ethers Seo-Jung Han, Gabriel Fernando de Melo, and Brian M. Stoltz* The Warren and Katharine Schlinger Laboratory

More information

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods

Synthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods Synthesis and Use of QCy7-derived Modular Probes for Detection and Imaging of Biologically Relevant Analytes Supplementary Methods Orit Redy a, Einat Kisin-Finfer a, Shiran Ferber b Ronit Satchi-Fainaro

More information

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol

An Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL

More information

How to build and race a fast nanocar Synthesis Information

How to build and race a fast nanocar Synthesis Information How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,

More information

Supplementary Information

Supplementary Information Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)

More information

Total Syntheses of Aflavazole and 14-Hydroxyaflavinine

Total Syntheses of Aflavazole and 14-Hydroxyaflavinine Electronic Supporting Information Total Syntheses of Aflavazole and 14-Hydroxyaflavinine Hailong Li, Qifeng Chen, Zhaohong Lu, and Ang Li* State Key Laboratory of Bioorganic and Natural Products Chemistry,

More information

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S

Supporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS

More information

Supporting Information for

Supporting Information for Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,

More information

Facile Synthesis of Flavonoid 7-O-Glycosides

Facile Synthesis of Flavonoid 7-O-Glycosides Facile Synthesis of Flavonoid 7-O-Glycosides Ming Li, a Xiuwen Han, a Biao Yu b * a State Key Laboratory of Catalyst, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China

More information

Electronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2012

Electronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2012 Ring Expansion of Alkynyl Cyclopropanes to Highly substituted Cyclobutenes via a N-Sulfonyl-1,2,3-Triazole Intermediate Renhe Liu, Min Zhang, Gabrielle Winston-Mcerson, and Weiping Tang* School of armacy,

More information

Enantioselective Conjugate Addition of 3-Fluoro-Oxindoles to. Vinyl Sulfone: An Organocatalytic Access to Chiral. 3-Fluoro-3-Substituted Oxindoles

Enantioselective Conjugate Addition of 3-Fluoro-Oxindoles to. Vinyl Sulfone: An Organocatalytic Access to Chiral. 3-Fluoro-3-Substituted Oxindoles Enantioselective Conjugate Addition of 3-Fluoro-Oxindoles to Vinyl Sulfone: An Organocatalytic Access to Chiral 3-Fluoro-3-Substituted Oxindoles Xiaowei Dou and Yixin Lu * Department of Chemistry & Medicinal

More information

Supporting Information

Supporting Information Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry

More information

Supporting Information

Supporting Information Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook

More information

Halogen halogen interactions in diiodo-xylenes

Halogen halogen interactions in diiodo-xylenes Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society

More information

Curtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes

Curtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes Supporting Information Curtius-Like Rearrangement of Iron-itrenoid Complex and Application in Biomimetic Synthesis of Bisindolylmethanes Dashan Li,, Ting Wu,, Kangjiang Liang,, and Chengfeng Xia*,, State

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction Magnus Rueping, * Erli Sugiono and Cengiz Azap General: Unless otherwise

More information

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol.

Supporting Information. (1S,8aS)-octahydroindolizidin-1-ol. SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.

More information

Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline

Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Chunpu Li 1,2, Lei Zhang 2, Shuangjie Shu 2 and Hong Liu* 1,2 Address: 1 Department of Medicinal

More information

An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters

An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters S1 An unusual dianion equivalent from acylsilanes for the synthesis of substituted β-keto esters Chris V. Galliford and Karl A. Scheidt* Department of Chemistry, Northwestern University, 2145 Sheridan

More information

Hai-Bin Yang, Xing Fan, Yin Wei,* Min Shi*

Hai-Bin Yang, Xing Fan, Yin Wei,* Min Shi* Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Solvent-controlled Nucleophilic Trifloromethylthiolation of Morita- Baylis-Hillman

More information

Supporting Information

Supporting Information Supporting Information Efficient Short Step Synthesis of Corey s Tamiflu Intermediate Nsiama Tienabe Kipassa, Hiroaki kamura, * Kengo Kina, Tetsuo Iwagawa, and Toshiyuki Hamada Department of Chemistry

More information

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane

Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Synthesis of borinic acids and borinate adducts using diisopropylaminoborane Ludovic Marciasini, Bastien Cacciuttolo, Michel Vaultier and Mathieu Pucheault* Institut des Sciences Moléculaires, UMR 5255,

More information

Supporting Information

Supporting Information 1 A regiodivergent synthesis of ring A C-prenyl flavones Alberto Minassi, Anna Giana, Abdellah Ech-Chahad and Giovanni Appendino* Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche

More information

Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures

Department of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures Supporting Information Low Temperature n-butyllithium-induced [3,3]-Sigmatropic Rearrangement/Electrophile Trapping Reactions of Allyl-1,1- Dichlorovinyl Ethers. Synthesis of - - and -lactones. Aaron Christopher

More information

Supporting Information

Supporting Information Meyer, Ferreira, and Stoltz: Diazoacetoacetic acid Supporting Information S1 2-Diazoacetoacetic Acid, an Efficient and Convenient Reagent for the Synthesis of Substituted -Diazo- -ketoesters Michael E.

More information

Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles

Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Supporting Information for Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu

More information

Electronic Supplementary Material

Electronic Supplementary Material Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly

More information

Supporting Information - I: Experimental Procedures and Characterization

Supporting Information - I: Experimental Procedures and Characterization Supporting Information - I: Experimental Procedures and Characterization The Direct Reductive Amination of Electron-deficient Amines with Aldehydes: the Unique Reactivity of Re 2 O 7 Catalyst 1 Braja Gopal

More information

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins

Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of

More information

The all-photochemical Synthesis an. OGP (10-14) Precursor

The all-photochemical Synthesis an. OGP (10-14) Precursor SUPPORTING INFORMATION The all-photochemical Synthesis an OGP (10-14) Precursor Jean-Luc Débieux, Christian G. Bochet* Department of Chemistry, University of Fribourg, 9 Chemin du Musée, CH-1700 Fribourg,

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Palladium-Catalyzed Regio-selective xidative C-H

More information

Supporting Information

Supporting Information Supporting Information Construction of Highly Functional α-amino itriles via a ovel Multicomponent Tandem rganocatalytic Reaction: a Facile Access to α-methylene γ-lactams Feng Pan, Jian-Ming Chen, Zhe

More information

Phil S. Baran*, Jeremy M. Richter and David W. Lin SUPPORTING INFORMATION

Phil S. Baran*, Jeremy M. Richter and David W. Lin SUPPORTING INFORMATION Direct Coupling of Pyrroles with Carbonyl Compounds: Short, Enantioselective Synthesis of (S)-Ketorolac Phil S. Baran*, Jeremy M. Richter and David W. Lin SUPPRTIG IFRMATI General Procedures. All reactions

More information

Qile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas,

Qile Wang, and Nan Zheng* Department of Chemistry and Biochemistry, University of Arkansas. Fayetteville, Arkansas, Supporting Information A Photocatalyzed Synthesis of Naphthalenes by Using Aniline as a Traceless Directing Group in [4+2] Annulation of AminoBenzocyclobutenes with Alkynes Qile Wang, and Nan Zheng* Department

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany Engineering Polymeric Chiral Catalyst Using Hydrogen Bonding and Coordination Interactions Lei Shi, 1,2 Xingwang Wang, 1 Christian A. Sandoval,

More information

A Sumanene-based Aryne, Sumanyne

A Sumanene-based Aryne, Sumanyne A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871

More information

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A

Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:

More information

for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl Compounds by Iminoiodanes

for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl Compounds by Iminoiodanes 10.1071/CH16580_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(4), 430-435 Supplementary Material for Brønsted Base-Mediated Aziridination of 2- Alkyl Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-1,4-Dicarbonyl

More information

Bulletin of the Chemical Society of Japan

Bulletin of the Chemical Society of Japan Supporting Information Bulletin of the Chemical Society of Japan Enantioselective Copper-Catalyzed 1,4-Addition of Dialkylzincs to Enones Followed by Trapping with Allyl Iodide Derivatives Kenjiro Kawamura,

More information

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in

1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow

More information

Electronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective

Electronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective Electronic Supplementary Information for A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective and Sensitive Detection of H 2 S: Synthesis, Spectra and Bioimaging Changyu Zhang, 1 Runyu Wang,

More information

A Strategy Toward the Synthesis of C 13 -Oxidized Cembrenolides

A Strategy Toward the Synthesis of C 13 -Oxidized Cembrenolides A Strategy Toward the Synthesis of C 13 -xidized Cembrenolides Alec Saitman, Steven D. E. Sullivan and Emmanuel A. Theodorakis* Department of Chemistry and Biochemistry, University of California, San Diego,

More information

Dual Catalyst System provides the Shortest Pathway for l-menthol Synthesis

Dual Catalyst System provides the Shortest Pathway for l-menthol Synthesis Chemical Communications Supporting Information Dual Catalyst System provides the Shortest Pathway for l-menthol Synthesis Hironori Maeda, Shinya Yamada, Hisanori Itoh, and Yoji Hori* Takasago International

More information

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002

Supporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002 Supporting Information for Angew. Chem. Int. Ed. Z50016 Wiley-VCH 2002 69451 Weinheim, Germany Total Synthesis of (±)-Wortmannin Takashi Mizutani, Shinobu Honzawa, Shin-ya Tosaki, and Masakatsu Shibasaki*

More information

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes

Significant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes Significant improvement of dye-sensitized solar cell performance by a slim phenothiazine based dyes Yong Hua, a Shuai Chang, b Dandan Huang, c Xuan Zhou, a Xunjin Zhu, *a,d Jianzhang Zhao, c Tao Chen,

More information

Supplementary Information (Manuscript C005066K)

Supplementary Information (Manuscript C005066K) Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)

More information

Supporting Information

Supporting Information Supporting Information Iron-catalyzed three-component reaction: multiple C-C bond cleavages and reorganizations Peng Wang, Saihu Liao, Jian-Bo Zhu, Yong Tang* State Key Laboratory of Organometallic Chemistry,Shanghai

More information

Supporting Information

Supporting Information Supporting Information Towards Singlet Oxygen Delivery at a Measured Rate: A Selfreporting Photosensitizer Sundus Erbas-Cakmak #, Engin U. Akkaya # * # UNAM-National Nanotechnology Research Center, Bilkent

More information

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol

Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol S1 Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2010 Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol Julien

More information

Supporting Information

Supporting Information Intramolecular hydrogen-bonding activation in cysteines. New effective radical scavenging Luisa Haya, a Iñaki Osante, b Ana M. Mainar, a Carlos Cativiela, b Jose S. Urieta*,a a Group of Applied Thermodynamics

More information

Supporting Information:

Supporting Information: Enantioselective Synthesis of (-)-Codeine and (-)-Morphine Barry M. Trost* and Weiping Tang Department of Chemistry, Stanford University, Stanford, CA 94305-5080 1. Aldehyde 7. Supporting Information:

More information

A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one

A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one A Facile and General Approach to 3-((Trifluoromethyl)thio)- 4H-chromen-4-one Haoyue Xiang and Chunhao Yang* State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy

More information

Synthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis

Synthesis of Secondary and Tertiary Amine- Containing MOFs: C-N Bond Cleavage during MOF Synthesis Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Synthesis of Secondary and Tertiary Amine- Containing MFs: C-N Bond

More information

Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene

Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Seyoung Choi and Sangho Koo* Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea. E-mail:

More information

PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions

PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions S1 Supporting Information PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions Yanan Zhao, a Jian Li, a Chunju Li, a Kun Yin, a Dongyan Ye a and Xueshun Jia*, a, b a Department

More information

Total Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig. M. Williams. Supporting Information

Total Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig. M. Williams. Supporting Information Total Synthesis of (±)-Vibsanin E. Brett D. Schwartz, Justin R. Denton, Huw M. L. Davies and Craig M. Williams Supporting Information General Methods S-2 Experimental S-2 1 H and 13 C NMR Spectra S-7 Comparison:

More information

Highly stereocontrolled synthesis of trans-enediynes via

Highly stereocontrolled synthesis of trans-enediynes via Supporting Information for Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes Tsutomu Konno*, Misato Kishi, and Takashi Ishihara Address: Department of Chemistry

More information

Regioselective Synthesis of the Tricyclic Core of Lateriflorone

Regioselective Synthesis of the Tricyclic Core of Lateriflorone Regioselective Synthesis of the Tricyclic Core of Lateriflorone Eric J. Tisdale, Hongmei Li, Binh G. Vong, Sun Hee Kim, Emmanuel A. Theodorakis* Department of Chemistry and Biochemistry, University of

More information

Supporting Information

Supporting Information Supporting Information Wiley-VC 2008 69451 Weinheim, Germany SI-1 A Concise Approach to Vinigrol Thomas J. Maimone, Ana-Florina Voica, and Phil S. Baran* Contribution from the Department of Chemistry,

More information

SUPPORTING INFORMATION. Fathi Elwrfalli, Yannick J. Esvan, Craig M. Robertson and Christophe Aïssa

SUPPORTING INFORMATION. Fathi Elwrfalli, Yannick J. Esvan, Craig M. Robertson and Christophe Aïssa Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 SUPPORTING INFORMATION S1 Fathi Elwrfalli, Yannick J. Esvan, Craig M. Robertson and Christophe

More information

Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine

Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine Ying Xie, a Hongjie Pan, a Xiao Xiao, a Songlei Li a and Yian Shi* a,b a Beijing National Laboratory for

More information

Supporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B

Supporting Information. Expeditious Construction of the DEF Ring System of Thiersinine B Supporting Information Expeditious Construction of the DEF Ring System of Thiersinine B Masaru Enomoto and Shigefumi Kuwahara* Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural

More information

Supporting Information

Supporting Information Supporting Information Enantioselective Synthesis of 3-Alkynyl-3-Hydroxyindolin-2-ones by Copper-Catalyzed Asymmetric Addition of Terminal Alkynes to Isatins Ning Xu, Da-Wei Gu, Jing Zi, Xin-Yan Wu, and

More information

Reactions. James C. Anderson,* Rachel H. Munday. School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK

Reactions. James C. Anderson,* Rachel H. Munday. School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK Vinyl-dimethylphenylsilanes as Safety Catch Silanols in Fluoride free Palladium Catalysed Cross Coupling Reactions. James C. Anderson,* Rachel H. Munday School of Chemistry, University of Nottingham, Nottingham,

More information

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials

Supporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde

More information

A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media

A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media Supplementary Information A fluorinated dendritic TsDPEN-Ru(II) catalyst for asymmetric transfer hydrogenation of prochiral ketones in aqueous media Weiwei Wang and Quanrui Wang* Department of Chemistry,

More information

A Total Synthesis of Paeoveitol

A Total Synthesis of Paeoveitol A Total Synthesis of Paeoveitol Lun Xu, Fengyi Liu, Li-Wen Xu, Ziwei Gao, Yu-Ming Zhao* Key Laboratory of Applied Surface and Colloid Chemistry of MOE & School of Chemistry and Chemical Engineering, Shaanxi

More information

Supporting Information

Supporting Information Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy

More information

Supplementary Figures

Supplementary Figures Supplementary Figures Supplementary Figure 1. Ainsliadimer A (1) inhibited I B phosphorylation in spleen extracts. The mice were received intravenous injection of DMSO, 1 (25 mg/kg) or BMS-345541 (25 mg/kg)

More information

Electronic Supplementary Information. An Ultrafast Surface-Bound Photo-active Molecular. Motor

Electronic Supplementary Information. An Ultrafast Surface-Bound Photo-active Molecular. Motor This journal is The Royal Society of Chemistry and wner Societies 2013 Electronic Supplementary Information An Ultrafast Surface-Bound Photo-active Molecular Motor Jérôme Vachon, [a] Gregory T. Carroll,

More information

Supplementary Material

Supplementary Material 10.1071/CH13324_AC CSIRO 2013 Australian Journal of Chemistry 2013, 66(12), 1570-1575 Supplementary Material A Mild and Convenient Synthesis of 1,2,3-Triiodoarenes via Consecutive Iodination/Diazotization/Iodination

More information

Flaws in foldamers: screw- sense fidelity and signal decay in achiral helical peptide oligomers

Flaws in foldamers: screw- sense fidelity and signal decay in achiral helical peptide oligomers Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2015 Flaws in foldamers: screw- sense fidelity and signal decay in achiral helical peptide oligomers

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2011 69451 Weinheim, Germany Enantioselective Total Synthesis of ( )-Jiadifenolide** Jing Xu, Lynnie Trzoss, Weng K. Chang, and Emmanuel A. Theodorakis* anie_201100313_sm_miscellaneous_information.pdf

More information

Supporting Information

Supporting Information ne-pot synthesis of pyrrolidino- and piperidinoquinolinones by three-component aza-diels Alder reactions of -arylimines with in situ generated cyclic enamides. Wenxue Zhang, Yisi Dai, Xuerui Wang, Wei

More information

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Visible light-mediated dehydrogenative

More information

Supporting Information

Supporting Information Supporting Information Catalytic Site-selective Acylation of Carbohydrates Directed by Cation-n Interaction Guozhi Xiao, 1 Gabriel A. Cintron-Rosado, 2 Daniel A. Glazier, 1,3 Bao-min Xi, 1, Can Liu, 1

More information