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

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1 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 Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 651, China Key Laboratory of Medicinal Chemistry for atural Resources, Ministry of Education, Yunnan University, Kunming 6591, China University of Chinese Academy of Sciences, Beijing 49, China List of Supporting Information 1. General Information... S2 2. Preparation of acyl hydroxamates... S2 3. Iron(II)-Catalyzed Curtius-like Rearrangement... S5 4. Biomimetic Synthesis of Bisindolylmethanes... S9 5. Copies of 1 MR and 13 C MR spectra.... S15 S1

2 1. General Information All reactions were performed in oven-dried round-bottom flasks. C 2 Cl 2 was refluxed with Ca 2. All reagents were used from commercial sources without further purifications, unless otherwise noted. The silica gel (- meshes) was used for column chromatography. Thin layer chromatographies (TLC) were carried out on GF254 plates (.25 mm layer thickness). Visualization of the developed chromatogram was performed by fluorescence quenching or by ceric ammonium molybdate stain. Yields reported were for isolated, spectroscopically pure compounds. 1 MR and 13 C MR experiments were performed on Bruker AM- spectrometer at ambient temperature. The residual solvent protons ( 1 ) or the solvent carbons ( 13 C) were used as internal standards. 1 MR data were presented as follows: chemical shift in ppm downfield from tetramethylsilane (multiplicity, coupling constant, integration). Chemical shifts (δ) were given in ppm with reference to solvent signals [ 1 MR: CDCl 3 (7.26), Acetone-d6 (5); 13 C MR: CDCl 3 (77.16), Acetone-d6 (29.84, 6.26)]. The following abbreviations are used in reporting MR data: s, singlet; br s, broad singlet; d, doublet; t, triplet; dd, doublet of doublets; m, multiplet. RMS (ESI) was taken on Agilent 65 Q-TF spectrometer. 2. Preparation of acyl hydroxamates At room temperature, CDI (2 eq.) was added to a solution of carboxylic acids (1 eq.) in DMF (2 ml/mmol). The reaction mixture was stirred for h and then - 2. Cl (4 eq.) was added. After being stirred for overnight at room temperature, 2 was added and the reaction system was stirred for another 15 min, and then diluted with EtAc and water. The aqueous phase was extracted with EtAc three times and the combined organic phases were washed with brine, dried over anhydrous a 2 S 4, filtered and concentrated in vacuo to afford the crude product hydroxamates. To a solution of the obtained hydroxamates (1 eq.) and benzoic acids (1 eq.) in C 2 Cl 2 ( ml/mmol), DCC (1 eq.) in C 2 Cl 2 (3 ml/mmol) was added dropwise at C. After being stirred for h, the reaction mixture was diluted by Et 2 (15 ml/mmol).the byproduct precipitated out and was removed by filtration. C 2 Cl 2 was removed under vacuum and the residue was purified by silica gel flash column chromatography (petroleum ether / acetone = 6 : 1) to afford acyl hydroxamates. Compound 9a. White foam in 2 mg, 86% yield. 1 MR ( Mz, CDCl 3 ) δ 9.27 (s, 1), 8.16 (d, J = z, 1), 4 (d, J = z, 2), (m, 3), 7.44 (t, J = z, 2), 7.35 (t, J = z, 1), 7.28 (t, J = z, 1), 3.82 (s, 2), S2

3 1.67 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 168.1, 164.8, 149.6, 135.7, 134.4, 1.1, 129.7, 128.8, 126.6, 125.2, 125.1, 123.1, 119.2, 11, 112.1, 84.1,.8, R-ESI-MS (m/z): calcd. for C a [M+a] +, , found Compound 9b. White powder in 1.29 g, 8% yield. 1 MR ( Mz, CDCl 3 ) δ 9.16 (br s, 1), 8.16 (d, J = z, 1), 7.91 (d, J = z, 1), 7.65 (s, 1), 7.6 (d, J = z, 1), 7.48 (d, J = 1.2 z, 1), 7.36 (t, J = z, 1), (m, 2), 3.82 (s, 2), 1.67 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 168.4, 162.8, ,.1, 135.9, 135.7, 133.1, 131.4, 129.7, 127.4, 125.3, 125.2, 124.7, 123.2, 119.1, 115.6, 111.8, 84.2,.8, C 22 C l2 2 5 a [M+a] +, 48641, found Compound 9c. White powder in 2.87 g, 75% yield. 1 MR ( Mz, CDCl 3 ) δ 9.23 (br s, 1), 8.46 (s, 2), 8.14 (d, J = z, 1), 8. (s, 1), 7.66 (s, 1), 7.6 (d, J = z, 1), 7.36 (t, J = z, 1), 7.29 (t, J = z, 1), 3.84 (s, 2), 1.67 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 16, 16, 149.6, 135.7, 133.2, 132.9, 132.6, 132.2, 1.2, 1.2, 12, 128.9, 127.7, 127.7, 127.7, 127.6, 125.3, 125.3, 124.1, 123.3, 121.3, 119.1, 115.6, 111.7, 84.4,.7, R-ESI-MS (m/z): calcd. for C 24 F a [M+a] +, , found Compound 18. White powder in 1.15 g, % yield. 1 MR ( Mz, CDCl 3 ) δ 8.93 (br s, 1), (s, 2), 8.13 (s, 1), (m, 5), 3.75 (s, 2). 13 C MR ( Mz, CDCl 3 ) δ 162.6, 133.3, 13, 132.7, 132.6, 132.3, 1.2, 12, 129.4, 12, 128.1, 127.8, 127.8, 127.7, 124.1, 121.4, 4. R-ESI-MS (m/z): calcd. for C F 6 3 [M+] +, 39716, found Compound S1. White powder in 2.99 g, 7 % yield. 1 MR ( Mz, Acetone-d 6 ) δ.19 (br s, 1), 7 (s, 2), 8.43 (s, 1), 7.68 (d, J = z, 1), 7. (d, J = z, 1), 7.36 (s, 1), 7.12 (t, J = z, 1), 5 (t, J = z, 1), 3.85 (s, 2); 13 C MR ( Mz, Acetone-d 6 ) δ 17, 163.1, 137.6, 13, 133.1, 132.8, 132.4, 131.1, 1.82, 1.78, 128.4, 128.4, , 128.3, 125.2, 12, 124.8, 12, 122.4, S3

4 119.8, 119.6, 112.2, 112.1, 8.2,.4; R-ESI-MS (m/z): calcd. for C F [M+] +, 43825, found Compound S2. White powder in 9 g, 73 % yield. 1 MR ( Mz, Acetone-d 6,): δ (br s, 1), 6 (br s, 1), 7 (s, 2), 8.43 (s, 1), 7.46 (s, 1), (m, 2), 6.96 (d, J = z, 1), 3.81 (s, 2), 2.41 (s, 3); 13 C MR ( Mz, Acetone-d 6 ) δ.1, 163.1, 13, 13, 133.1, 132.8, 132.4, 131.1, 1.8, 1.8, 128.7, 128.6, 128.4, 125.3, 125.1, 124.9, 12, 12, 119.2, 111.9, 111.9, 7.7,.4, 21.7; R-ESI-MS (m/z): calcd. for C 15 F [M+] +, 44981, found Compound S3. White powder in 1.69 g, 86 % yield. 1 MR ( Mz, Acetone-d 6 ) δ (br s, 1),. (br s, 1), 7 (s, 2), 8.43 (s, 1), 7.87 (s, 1), 7.42 (s, 1), 7.38 (d, J = z, 1), 7.23 (dd, J =, z, 1), 3.84 (s, 2); 13 C MR ( Mz, Acetone-d 6 ) δ 169.7, 163.1, 136.2, 136.1, 13, 133.1, 132.8, 13, 13, 1.9, 1.8, 1.2, , , , 126.7, 12, 125.2, 12, 12, 122.3, 114.1, 11, 112.8, 8.2, 3; R-ESI-MS (m/z): calcd. for C BrF a [M+a] +, , found Compound S4. White powder in 1.46 g, 8 % yield. 1 MR ( Mz, Acetone- d 6 ) δ (br s, 1),.34 (br s, 1), 7 (s, 2), 8.43 (s, 1), 7.68 (d, J = z, 1), 7.45 (d, J = 1.3 z, 1), 7. (s, 1), 7-5 (m, 1), 3.84 (s, 2); 13 C MR ( Mz, Acetone-d 6 ) δ 169.8, 163.1, 137.9, 13, 133.1, 132.8, 13, 13, 1.8, 1.8, 128.8, 127.9, 127.2, 126.1, 12, 125.2, 12, 12, 1.2, 112, , 8.7,.2; R-ESI-MS (m/z): calcd. for C ClF [M+] +, 46435, found Compound S5. White powder in.996 g, 76% yield. 1 MR ( Mz, Acetone-d 6 ) S4

5 δ 12 (br s, 1), 4 (br s, 1), 4 (s, 2), 8.41 (s, 1), 7 (d, J = 7.2 z, 1), 7.28 (d, J = z, 1), 5- (m, 2), 3.79 (s, 2), 2.47 (s, 3); 13 C MR ( Mz, Acetone-d 6 ) δ.1, 163.1, 13, 134.7, 133.4, 133.1, 132.8, 132.4, 13, 1.8, 1.7, 129.6, 128.4, 128.3, 128.3, 127.9, 125.2, 12, 12, 119.7, 118.7, 111.2, 3.9, 29.3, 11.7; R-ESI-MS (m/z): calcd. for C 15 F [M+] +, 44981, found Compound S6. White powder in.71 g, 71% yield. 1 MR ( Mz, Acetone-d 6 ) δ (br s, 1), 4 (br s, 1), 7 (s, 2), 8.43 (s, 1), (m, 2), 7.21 (s, 1), 6.78 (dd, J =, 2.2 z, 1), 3.83 (s, 3), 3.81 (s, 2); 13 C MR ( Mz, Acetone-d 6 ) δ 163.1, 15, 13, 133.1, 132.8, 13, 131.1, 1.8, 1.8, , , , , 125.6, 12, 125.2, 12, 112.9, 112.8, 112.7, 7.9, 1.3, 55.9,.4; R-ESI-MS (m/z): calcd. for C 15 F [M+] +, 46931, found Iron(II)-Catalyzed Curtius-like Rearrangement Ar 1 R R = 3,5-( ) 2 -Bz Fe(Tf) 2 (15%) L1, Ar 2 2 C 2 Cl 2 Ar 1 Ar 2 L1 A solution of Fe(Tf) 2 (15 mmol) and L1 (3 mmol) in C 2 Cl 2 (2 ml) was stirred for h, after which time the resulting catalyst system solution was added to a solution of acyl hydroxamates (.1 mmol) and anilines (.2 mmol) in C 2 Cl 2 (2 ml) at room temperature. After being stirred for 8- h when all the starting material acyl hydroxamates was fully consumed, the reaction was quenched with saturated ac 3 aqueous solution, and the aqueous phase was extracted with EtAc three times. The combined organic layers were washed with brine and dried over anhydrous a 2 S 4, filtered, and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (petroleum ether / acetone = 6 : 1) to give ureas. S5

6 Table S1. Solvents ptimization entry solvent conversion (%) yield (%) 1 toluene 33 2 C 2 Cl TF 57 4 dioxane 41 5 MeC 57 6 TFE 69 7 FIP 69 8 DMF 65 9 DMS 65 Table S2. Catalysts ptimization entry Catalyst conversion (%) yield (%) 1-2 Fe(Tf) FeCl FeBr Fe(Ac) FeS K 4 Fe(C) 6 <1 trace 8 Fe(Tf 2 ) Zn(Tf) 2 Sc(Tf) 3 S6

7 Compound. Reaction time: 8 h. White powder in.9 mg, 85% yield. 1 MR ( Mz, CDCl 3 ) δ 8 (d, J = z, 1), 6 (d, J = z, 1), 7.47 (s, 1), 7. (t, J = z, 1), (m, 5), 6-3 (m, 1), 6.81 (s, 1), 5.25 (t, J = z, 1), (d, J = z, 2), 1.64 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 15, 149.7, 138.4, 135.8, 129.4, 129.3, 124.8, 124.2, 12, 122.9, 12, 119.3, 11, 115.4, 8, 35.7, R-ESI-MS (m/z): calcd. for C [M+] +, , found Compound 11. Reaction time: 8 h. White powder in 3 mg, 84% yield. 1 MR ( Mz, CDCl 3 ) δ 7 (d, J = z, 1), 3 (d, J = z, 1), 7.44 (s, 1), 7.28 (t, J = z, 1), 7.18 (t, J = z, 1), 8 (d, J = z, 2), 1 (d, J = z, 2), 6.84 (s, 1), 5.35 (t, J = z, 1), 4.45 (d, J = z, 2), 2.25 (s, 3), 1.63 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 156.4, 149.7, 135.8, 135.7, 13, 129.9, 129.4, 124.8, 123.9, 122.9, 12, 119.3, 118.2, 115.4, 83.9, 35.7, 28.3,.9. R-ESI-MS (m/z): calcd. for C a [M+a] +, , found Compound 12. Reaction time: 8 h. White powder in 31.8 mg, 78% yield. 1 MR ( Mz, CDCl 3 ) δ 9 (d, J = z, 1), 6 (d, J = z, 1), 7.41 (s, 1), 7. (t, J = z, 1), 7.21 (t, J = z, 1), 6.86 (s, 2), 5. (s, 1), 2 (s, 3), 2.23 (s, 3), 2.18 (s, 6), 1.64 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 15, 149.7, 137.9, 137.2, 135.8, 131.1, 129.6, 129.3, 124.8, 123.7, 122.8, 11, 118.6, 115.3, 83.7, 35. 7, 28.3, 2, R-ESI-MS (m/z): calcd. for C [M+] +, , found Compound 13. Reaction time: 8 h. White powder in 34.2 mg, 87% yield. 1 MR ( Mz, CDCl 3 ) δ 9 (d, J = z, 1), 7 (d, J = z, 1), 7.47 (s, 1), 7. (t, J = z, 1), 7.21 (t, J = z, 1), 7.12 (d, J = z, 2), 6.79 (d, J = S7

8 z, 2), 6.39 (s, 1), (br s, 1 ), 1 (d, J = 5.3 z, 2), 3.75 (s, 3), 1.64 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 157.3, 156.6, 149.7, 135.8, 1.7, 129.4, 125.2, 124.8, 12, 122.9, 119.4, 118.3, 115.4, 114.8, 83.9, 55.6, 35.8, R-ESI-MS (m/z): calcd. for C [M+] +, , found Compound 14. Reaction time: 8 h. White powder in 32.2 mg, 81% yield. 1 MR ( Mz, CDCl 3 ) δ 4 (d, J = z, 1), 7.46 (d, J = z, 1), 7.41 (s, 1), 7.27 (t, J = z, 1), 7.15 (t, J = z, 1), 7. (s, 4), 6.87 (s, 1), 5.31 (t, J = z, 1), 4.37 (d, J = z, 2), 1.62 (s, 9). 13 C MR (1 Mz, CDCl 3 ) δ 15, 149.7, 137.2, 135.7, 129.2, 128.7, 124.9, 123.9, 122.9, 121.8, 119.1, 117.8, 11, 84.1, 35.7, R-ESI-MS (m/z): calcd. for C Cl 3 3 a [M+a] +, , found Compound 15. Reaction time: 8 h. White powder in 35.7 mg, 8% yield. 1 MR ( Mz, CDCl 3 ) δ 8.11 (d, J = z, 1), 1 (dd, J =,.9 z, 1), 7.6 (d, J = z, 1), 5 (s, 1), 7.48 (dd, J =,.9 z, 1), 7.32 (t, J = z, 1), (m, 2), (m, 1), 6.79 (s, 1), 5.21 (br s, 1), 7 (d, J = z, 2), 1.65 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 155.3, 149.7, 136.6, 135.9, 132.6, 129.3, 12, 124.9, 124.8, 124.3, 12, 122.7, 119.3, 117.6, 11, 114.6, 8, 36.1, R-ESI-MS (m/z): calcd. for C Br 3 3 [M+] +, 44917, found Compound 16. Reaction time: 8 h. White powder in 3 mg, 77% yield. 1 MR ( Mz, CDCl 3 ) δ 8. (d, J = z, 1), 7.83 (d, J = z, 1), 7.72 (d, J = z, 1), 9 (d, J = z, 1), 3 (s, 1), 7.31 (t, J = z, 1), (m, 2), (m, 2), 5.41 (br s, 1), 4 (d, J = z, 2), 1.65 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 15, 149.7, 139.3, 139.2, 135.8, 129.4, 129.3, 125.7, 124.9, 124.2, 123.3, 122.9, 119.4, 117.8, 11, 92.1, 8, 3, R-ESI-MS (m/z): calcd. for C I 3 3 [M+] , found S8

9 Compound 17. Reaction time: 8 h. White powder in 3 mg, 79% yield. 1 MR ( Mz, CDCl 3 ) δ 3 (d, J = z, 1), 7.81 (d, J = z, 2), 1 (s, 1), 7.47 (d, J = z, 1), 7.41 (s, 1), 7. (d, J = z, 2), (m, 1), 7.13 (t, J = z, 1), 5.72 (t, J = z, 1), 4.41 (d, J = z, 2), 3.81 (s, 3), 1.61 (s, 9). 13 C MR ( Mz, CDCl 3 ) δ 167.2, 155.3, 149.7, 143.6, 135.7, 13, 129.2, 124.9, 12, , 119.1, 118.2, 117.7, 115.4, 84.1, 52.1, 35.6, R-ESI-MS (m/z): calcd. for C [M+] +, , found Compound. Reaction time: h. White powder in 11.6 mg, 51% yield. 1 MR ( Mz, Acetone-d6) δ (s, 1), 7.49 (d, J = z, 2), (m, 4), (m, 3), 6.91 (t, J = z, 1), 6.21 (br s, 1), 4.41 (d, J = z, 2). 13 C MR ( Mz, Acetone-d6) δ 156.1, 141.6, 141.4, 129.4, 129.2, 128.2, 127.6, 122.2, 118.9, 118.8, R-ESI-MS (m/z): calcd. for C [M+] +, , found Biomimetic Synthesis of Bisindolylmethanes A solution of Fe(Tf) 2 (15 mmol) and L1 (3 mmol) in C 2 Cl 2 (2 ml) was stirred for h, after which time the resulting catalyst system solution was added to a solution of acyl hydroxamates (.1 mmol) and indoles (.2 mmol) in C 2 Cl 2 (2 ml) at room temperature. After being stirred for 5 h when all the starting material acyl hydroxamates was fully consumed. the reaction was quenched with saturated ac 3 aqueous solution, and the aqueous phase was extracted with EtAc three times. The combined organic layers were washed with brine and dried over anhydrous a 2 S 4, filtered, and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (petroleum ether / EtAc = 6 : 1) to give bisindolylmethanes. Arundine (1). Slightly red powder in 17.8 mg, 72% yield. 1 MR ( Mz, CDCl 3 ) δ 7.89 (br s, 2), 7.63 (d, J = z, 2), 7.36 (d, J = z, 2), 7. (t, J = z, 2), 7. (t, J = z, 2), 6.94 (s, 2), 4.25 (s, 2); 13 C MR ( Mz, Acetone-d 6 ) δ 137.9, 128.7, 12, 121.9, 119.7, 119.2, 115.8, 11, 21.9; R-ESI-MS (m/z): calcd. for C K [M+K] +, 28789, found S9

10 Compound 3. Slightly red powder in 19.3 mg, 71% yield. 1 MR ( Mz, CDCl 3 ) δ 7.76 (br s, 2), 7.41 (s, 2), 7.23 (d, J = z, 2), 1 (d, J = z, 2), 6.86 (s, 2), 4.17 (s, 2), 2.43 (s, 6); 13 C MR ( Mz, CDCl 3 ) δ 134.9, 12, 127.9, 123.6, 122.6, 11, 115.3, 1.8, 21.6, 21.3; R-ESI-MS (m/z): calcd. for C K[M+K] +, , found Compound 4. Slightly red powder in 29.6 mg, 73% yield. 1 MR ( Mz, CDCl 3 ) δ 2 (br s, 2), 7.74 (s, 2), (m, 4), 6.99 (s, 2), 4.18 (s, 2); 13 C MR ( Mz, CDCl 3 ) δ 135.2, 129.3, 12, 123.6, , 11, 112.7, R-ESI-MS (m/z): calcd. for C Br 2 2 [M-] -,.9294, found Cl 5 Cl Compound 5. Slightly red powder in 23.7 mg, 75% yield. 1 MR ( Mz, CDCl 3 ) δ 7.91 (br s, 2), 7.47 (d, J = z, 2), 7.35 (d, J = 1.4 z, 2), 5 (dd, J =, 1.6 z, 2), 6.92 (s, 2), 4.18 (s, 2); 13 C MR ( Mz, CDCl 3 ) δ 136.9, 128.1, 126.2, 122.9, 1.2, 115.7, 111.2, 21.3; R-ESI-MS (m/z): calcd. for C Cl 2 2 [M-] -, 315, found 317. Compound 21. Slightly red powder in 18.1 mg, 66% yield. 1 MR ( Mz, Acetone-d 6 ) δ 9.75 (br s, 2), 7.34 (d, J = z, 2), 7.22 (d, J = z, 2), 6.93 (t, J = z, 2), 6.83 (t, J = 7.4 z, 2), 9 (s, 2), 2. (s, 6); 13 C MR ( Mz, Acetone-d 6 ) δ 136.6, 131.9, 1.1, 1.9, 11, , 111.2, 11, 19.9, 11.9; R-ESI-MS (m/z): calcd. for C K [M+K] +, , found Compound 22. Slightly red powder in.7 mg, 68% yield. 1 MR ( Mz, CDCl 3 ) δ 7.83 (br s, 2), 7.27 (d, J = z, 2), 9 (d, J = 2.1 z, 2), 6.93 (s, 2), 6.88 (dd, J =, 2.3 z, 2), 4.19 (s, 2), 3.84 (s, 6); 13 C MR ( Mz, CDCl 3 ) δ 15, 131.8, 128.1, 123.2, 11, 112.2, 111.9, 1.2, 56.1, 21.4; R-ESI-MS (m/z): calcd. for C K [M+K] +, 345., found S

11 Compound 23. Slightly red powder in 19.7 mg, 72% yield. 1 MR ( Mz, CDCl 3 ) δ 7.92 (br s, 1), 7.82 (br s, 1), 7.66 (d, J = z, 1), 7.39 (d, J = z, 1), 7.28 (s, 1), 7.22 (t, J = z, 1), 7.13 (t, J = z, 1), 8 (d, J = 2.2 z, 1), 6.95 (br s, 2), 6.88 (dd, J =, 2.3 z, 1), 4.24 (s, 2), 3.84 (s, 3); 13 C MR ( Mz, CDCl 3 ) δ 15, 136.6, 131.7, 128.1, 127.7, 123.2, 122.3, 122.1, 119.4, 119.3, 115.8, 11, 112.2, 111.9, 111.2, 1.2, 56.1, 21.4; R-ESI-MS (m/z): calcd. for C K [M+K] +, 31894, found Compound 24. Slightly red powder in 19.3 mg, 75% yield. 1 MR ( Mz, CDCl 3 ) δ 7.89 (br s, 1), 7.8 (br s, 1), 7.66 (d, J = z, 1), 7.44 (s, 1), 7.38 (d, J = z, 1), 7.28 (s, 1), 7.22 (t, J = z, 1), 7.13 (t, J = z, 1), 5 (d, J = z, 1), 6.92 (d, J =, 2), (m, 2), 2.46 (s, 3); 13 C MR ( Mz, CDCl 3 ) δ 136.6, 134.9, 12, 127.9, 127.7, 123.6, 12, 122.3, 12, 119.4, 119.3, 11, 115.9, 115.2, 111.2, 1.8, 21.6, 21.3; R-ESI-MS (m/z): calcd. for C K [M+K] +, 29945, found Compound 25. Slightly red powder in 1 mg, 72% yield. 1 MR ( Mz, CDCl 3 ) δ 7.89 (m, 2), 9 (d, J = z, 1), 7.36 (d, J = z, 1), (m, 2), 7.19 (t, J = z, 1), 9 (t, J = z, 1), 6.99 (s, 1), 6.95 (s, 1), 6.91 (dd, J =, 2.4 z, 1), 4.19 (s, 2); 13 C MR (Mz, CDCl 3 ) δ 15, 156.6, 136.6, 133.1, 127.6, 124.1, 122.3, 122.1, 119.4, 119.3, 115.4, 111.8, 111.7, 111.2, 11, 1.3, 4.4, 4.2, 21.4; R-ESI-MS (m/z): calcd. for C F 2 [M-] -, 269, found 269. Compound 26. Slightly red powder in 2 mg, 71% yield. 1 MR ( Mz, CDCl 3 ) δ 7.91 (br s, 2), 9 (d, J = z, 2), 7.36 (d, J = z, 1), 7.25 (d, J = 3.4 z, 1), 7.19 (t, J = z, 1), (m, 2), 6.95 (d, J = z, 2), 4.19 (s, 2); 13 C MR ( Mz, CDCl 3 ) δ 136.6, 134.9, 128.8, 127.6, 125.1, 123.7, 122.4, 122.3, 122.2, 119.4, 119.3, 118.9, 115.7, 115.4, 112.2, 111.2, 21.3; R-ESI-MS (m/z): calcd. for C Cl 2 K [M+K] +, 31399, found 35. S11

12 Compound 27. Slightly red powder in 2 mg, 71% yield. 1 MR ( Mz, CDCl 3 ) δ 7.89 (m, 2), 7.6 (d, J = z, 1), (d, J = z, 1), 7.37 (d, J = z, 1), 7.34 (d, J = 1.4 z, 1), 7. (t, J = z, 1), 7. (t, J = z, 1), 5 (dd, J =, 1.6 z, 1), 6.93 (s, 2), 4.22 (s, 2). 13 C MR ( Mz, CDCl 3 ) δ 136.9, 136.6, 12, 127.6, 126.3, 12, 122.3, 122.2, 1.3, 1.1, 119.4, 119.3, 11, 11, 111.2, 111.1, R-ESI-MS (m/z): calcd. for C Cl 2 K [M+K] +, 31399, found Compound 28. Slightly red powder in 2 mg, 77% yield. 1 MR ( Mz, CDCl 3 ) δ 7.95 (br s, 2), 7.77 (s, 1), 7.62 (d, J = z, 1), 7. (d, J = z, 1), (m, 3), 7.13 (t, J = z, 1), 6.97 (br s, 2), 4.22 (s, 2); 13 C MR ( Mz, CDCl 3 ) δ 136.6, 135.2, 12, 127.6, 124.9, 123.6, 122.3, 122.2, 12, 119.4, 119.3, 115.6, 115.3, 112.7, 112.6, 111.3, R-ESI-MS (m/z): calcd. for C Br 2 K [M+K] +, , found Compound 29. Slightly red powder in 25.2 mg, 68% yield. 1 MR ( Mz, Acetone-d 6 ) δ.16 (br s, 1), 9.96 (br s, 1), 7.94 (d, J =.6 z, 1), 6 (d, J = z, 1), (m, 2), 7.25 (d, J = z, 1), (m, 2), 7 (t, J = z, 1), 6.96 (t, J = z, 1), 4. (s, 2); 13 C MR ( Mz, Acetone-d 6 ) δ 137.9, 136.9, 131.4, 1.1, 128.6, 12, 124.8, 12, 12, 119.7, 119.3, 115.4, 11, 112.1, 82.2, R-ESI-MS (m/z): calcd. for C I 2 K [M+K] +, , found Compound. Slightly red powder in 14.4 mg, 5% yield. 1 MR ( Mz, Acetone-d 6 ) δ.68 (br s, 1), 2 (br s, 1), 7 (d, J = z, 1), 1 (dd, J =, 2.2 z, 1), 6 (t, J = z, 2), 7. (s, 1), 7.38 (d, J = z, 1), 7.21 (s, 1), 7 (t, J = z, 1), 6.96 (t, J = z, 1), 4.33 (s, 2); 13 C MR ( Mz, Acetone-d 6 ) δ 141.8,.9, 137.9, 12, 127.9, 127.3, 123.6, 122.1, 119.6, 119.4, 118.9, 117.4, 116.9, 11, 112.4, 112.2, 21.7; R-ESI-MS (m/z): calcd. for C K [M+K] +, 33639, found S12

13 Compound 31. Slightly red powder in 2 mg, 66% yield. 1 MR ( Mz, Acetone-d 6 ) δ.33 (br s, 1), 9.96 (br s, 1), 8.36 (s, 1), 7.79 (dd, J =, z, 1), 8 (d, J = z, 1), 7.45 (d, J = z, 1), 7.37 (d, J = z, 1), 7.23 (s, 1), 7.11 (s, 1), 8 (t, J = z, 1), 6.97 (t, J = z, 1), 4.28 (s, 2), 3.83 (s, 3); 13 C MR ( Mz, Acetone-d 6 ) δ, 168.4,.4, 137.9, 128.6, 128.2, 125.3, 12, 123.3, 122.6, 12, 121.6, 119.7, 119.3, 117.4, 11, 112.1, 111.9, 51.8, 21.8; R-ESI-MS (m/z): calcd. for C K [M+K] +, 34843, found Compound 32. Slightly red powder in 1 mg, 54% yield. 1 MR ( Mz, CDCl 3 ) δ 7.73 (m, 2), 7.66 (d, J = z, 1), 7.45 (d, J = z, 1), (m, 2), 7.18 (t, J = z, 1), (m, 2), 1 (t, J = z, 1), 6.68 (s, 1), 4.15 (s, 2), 2.37 (s, 3); 13 C MR ( Mz, CDCl 3 ) δ 136.6, 135.4, 131.4, 129.2, 127.6, 122.2, 12, 12, 119.3, 119.2, 11, 118.7, 116.4, 111.2, 11, 1.2,.1, R-ESI-MS (m/z): calcd. for C K [M+K] +, 29945, found Ph 33 Compound 33. Slightly red powder in 2 mg, 71% yield. 1 MR ( Mz, CDCl 3 ) δ 4 (br s, 1), 7.76 (br s, 1), 7.67 (d, J = z, 1), 4- (m, 3), (m, 5), (m, 2), 7.14 (t, J = z, 1), 6 (t, J = z, 1), 6.63 (s, 1), 4.32 (s, 2). 13 C MR ( Mz, CDCl 3 ) δ 136.7, 136.2, 13, 133.1, 129.8, 129.1, , , 12, 122.6, 12, 122.1, 119.9, 119.8, 119.3, 119.1, 116.4, 111.6, 111.2, 1.9,.8. R-ESI-MS (m/z): calcd. for C K [M+K] +, , found Compound 34. Slightly red powder in 2 mg, 68 % yield. 1 MR ( Mz, Acetone-d 6 ) δ 4 (br s, 1), 9.88 (br s, 1), 5 (d, J = z, 1), 7. (d, J = 1.4 z, 1), 7.35 (d, J = z, 1), 7.26 (d, J = z, 1), 6 (t, J = z, 1), (m, 3), 4.14 (s, 2), 2.46 (s, 3); 13 C MR ( Mz, Acetone-d 6 ) δ 137.9, 135.1, 13, 131.2, 12, 124.4, 123.3, 12, 1.9, 11, 119.3, 118.3, 115.9, 112.4, 112.1, 1.9,.6, 11.8; R-ESI-MS (m/z): calcd. for C Cl 2 K [M+K] +, 33555, found S13

14 Compound 35. Slightly red powder in 1 mg, 75% yield. 1 MR ( Mz, CDCl 3 ) δ 7.89 (br s, 1), 7.64 (dd, J =, z, 2), 7.37 (d, J = z, 1), 7. (d, J = z, 1), (m, 2), (m, 2), 6.95 (s, 1), 6.79 (s, 1), 4.25 (s, 2), 3.71 (s, 3); 13 C MR ( Mz, CDCl 3 ) δ 137.3, 136.6, 128.1, 127.7, 127.1, 122.3, 12, 121.6, , 119., 119.3, 118.7, 116.1, 114.3, 111.2, 9.2, 32.7, R-ESI-MS (m/z): calcd. for C K [M+K] +, 29945, found Compound 36. Slightly red powder in 2 mg, 73 % yield. 1 MR ( Mz, CDCl 3 ) δ 7.76 (br s, 1), 4 (dd, J =, z, 2), 7.26 (d, J = z, 1), (m, 4), 9 (dd, J = z, 2), (m, 4), 6.83 (d, J = z, 2), 5.15 (s, 2), 4.17 (s, 2); 13 C MR ( Mz, CDCl 3 ) δ 13, 13, 136.6, 128.8, 128.4, 127.7, 127.6, 126.8, 126.7, 122.3, 12, 121.8, 119.6, 119.4, 119.3, 11, 115.9, 114.9, 111.2, 9.8, 5, 21.4; R-ESI-MS (m/z): calcd. for C [M+] +, , found S14

15 5. Copies of 1 MR and 13 C MR spectra Boc 9a Boc 9a S15

16 S Boc Cl Cl 9b Boc Cl Cl 9b

17 S Boc 9c Boc 9c

18 S

19 S S1 S1

20 S S2 S2

21 S S3 Br S3 Br

22 S S4 Cl S4 Cl

23 S S5 S5

24 S S6 Me S6 Me

25 S Boc Boc

26 S Boc 11 Boc 11

27 S Boc 12 Boc 12

28 S Boc Me 13 Boc Me 13

29 S Boc Cl 14 Boc Cl 14

30 S Boc Br 15 Boc Br 15

31 S Boc I 16 Boc I 16

32 S Boc C 2 Me 17 Boc C 2 Me 17

33 S

34 S Arundine (1) Arundine (1)

35 S

36 S Br Br 4 Br Br 4

37 S Cl Cl 5 Cl Cl 5

38 S

39 S Me Me 22 Me Me 22

40 S Me 23 Me 23

41 S

42 S F 25 F 25

43 S Cl 26 Cl 26

44 S Cl 27 Cl

45 S Br 28 Br 28

46 S I 29 I 29

47 S

48 S C 2 Me 31 C 2 Me 31

49 S

50 S Ph 33 Ph 33

51 S Cl 34 Cl 34

52 S

53 S Bn 36 Bn 36

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