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1 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 Zhang * State Key Laboratory of Applied rganic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, Gansu, , People s Republic of China zhangwei6275@lzu.edu.cn Supporting Information Content General Experimental procedures References Analytical data for compounds 5a-5o Analytical data for compounds 6a-6f 1 and 13 C spectra page S2 S2-S3 S3 S2-S9 S10-S12 S13-S39 1

2 General remark: All reagents were purchased from commercial suppliers and used without further purification. Flash chromatography was carried out with silica gel ( mesh). Analytical TLC was performed with silica gel GF254 plates, and the products were visualized by UV detection. 1 MR and 13 C MR (400 Mz and 100Mz, respectively) spectra were recorded in CDCl 3. Chemical shifts (δ) are reported in ppm using TMS as internal standard and spin-spin coupling contants (J) are given in z. The high resolution mass spectra (RMS) were measured on a Bruker Daltonics APEXⅡ47e spectrometer by ESI. Mp data were measured with micro melting point apparatus. The X-ray crystallographic analysis was performed with a Siemens SMART CCD and a Siemens P4 diffractometer Experimental procedures: General procedure for the preparation of 5-hydropyrrolidin-2-ones 3a, 3b, 3c: A 50 ml round-bottom flask was charged with -benzylmaleimide (346 mg, 2 mmol), CeCl (746 mg, 2 mmol), anydrous Me (10 ml), and a stirbar. The flask was cooled to 0, after 5 mintues, ab 4 (76 mg, 2 mmol) was added portionwise over 5-10 min, icl (474 mg, 2 mmol) added immediately 1, additional ab 4 (76 mg, 2 mmol) were added, the mixture was stirred for 5 minutes at 0, 10 ml water poured into the flask, and the mixture extracted with ethyl acetate (3x30 ml). The combined organic layers were dried with anhydrous a 2 S 4, filtered, and concentrated in vacuo. The residue was isolated by silica gel column chromatography to give a white solid 300 mg (85%). 3b: yield 75%, 3c: yield 20%. The preparation of 6-hydroxypiperidin-2-ones 4a 2 : A 100 ml round-bottom flask was charged with - benzyl -glutarimide (200 mg, mmol), anhydrous Me (41.3 ml), and a stirbar. The flask was cooled to 0 C. ab 4 (942 mg, 24.8 mmol) was added portionwise over 5 10 min. The reaction was stirred vigorously for 2 h at 0 C. Conversion was measured by TLC (hexane-actone 4:1). If all starting material was not consumed after 2 h, 10 additional equiv ab 4 were added every 30 minutes, until full conversion was realized. Upon complete conversion of the imide, the reaction mixture was poured onto virgorously stirring 200 ml 1:1 C 2 Cl 2 /ac 3 (sat. aq.) which had been pre-cooled to 0 C. The biphasic slurry was stirred at 0 C for 5 minutes, and the layers partitioned in a separatory funnel. The aqueous layer was extracted with C 2 Cl 2 (2 25 ml). The combined organic layers were dried over a 2 S 4, filtered, and concentrated in vacuo. The residue was isolated by silica gel column chromatography to get the product as a white solid 200 mg (85%). 2

3 General procedure for the Pyrrolidino- and Piperidinoquinolinones. sythesis of compounds 5a-5o, 6a-6f. Aromatic aldehyde (1.1 mmol ) and anilines (1.0 mmol ) were dissolved in anhydrous C 2 Cl 2 (20 ml), and 0.5 g 4 Å molecule sieves was added. The mixture was stirred at room temperature for 2 hrs, The (1.0 mmol 5-hydropyrrolidin-2-ones or 6-hydroxypiperidin-2-ones and 0.8 mmol BF 3 Et 2 were added, respectively. The mixture was stirres for another 2 h, 10 ml water was added, and the resulting mixture was extracted with C 2 Cl 2 (3 30). The organic phase was dried over a 2 S 4, filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography (hexane-acetone) to give the desired products. References: (1) D. Dhawan, S. K. Grover, Synth. Commun., 1992, 22, (2) Izzat T. Raheem, Parvinder S. Thiara, and Eric. Jacobsen J. Am. Chem. Soc., 2007, 129,

4 Analytical data for compounds 5a-5o, 6a-6f: exo-5a 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.28 (d, J = 8.8z, 2), 7.66 (d, J = 8.8z, 2), 7.43 (t, J = 8.0z, 2), 7.35 (d, J = 7.6z, 2), 7.29 (d, J = 7.2z, 1), (m, 1), 6.72 (d, J = 8.0z, 1), (m, 1), 5.66 (d, J = 8.0z, 1), 4.75 (d, J = 2.4z, 1), 3.96 (s, 1), (m, 1), 3.08 (dd, J = 11.6, 16z, 1), 2.02 (dd, J = 8.0, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 172.4, 147.8, 147.8, 144.3, 138.3, 129.3, 128.9, 127.4, 126.4, 125.6, 124.2, 120.9, 119.6, 116.3, 59.9, 57.5, 40.6, 30.5 ppm. ESI-RMS: m/z Calcd for C : , found endo-5a 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.24 (d, J = 8.4z, 2), 7.64 (d, J = 8.4z, 2), 7.36 (t, J = 6.8z, 3), 7.07 (d, J = 7.2z, 3), 6.64 (d, J = 8.0z, 1), (m, 2), 5.04 (d, J = 5.6z, 1), 4.38 (d, J = 9.2z, 1), 4.31 (s, 1), (m, 1), 2.72 (dd, J = 7.6, 16.8z, 1), 2.34 (dd, J = 2.4, 16.8z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.2, 148.5, 147.9, 137.0, 131.8, 129.5, 129.2, 128.9, 128.2, 127.7, 124.0, 117.9, 116.5, 114.9, 50.5, 56.2, 38.7, 34.9 ppm. ESI-RMS: m/z Calcd for C : , found exo-5b C 3 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.25 (d, J = 8.8z, 2), 7.65 (d, J = 8.8z,2), (m, 3), 7.09 (dd, J = 1.6, 3.6z, 2), 6.89 (dd, J = 1.6, 8.0z, 1), 4

5 6.57 (d, J = 8.00z, 1), 6.16 (d, J = 1.2z, 1), 4.99 (d, J = 5.6z, 1), 4.36 (d, J = 9.2z, 1), 4.17 (s, 1), (m, 1), 2.48 (dd, J = 7.2, 16.8z, 1), 2.35 (dd, J = 2.4, 17.2z, 1), 1.95 (s, 3) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.3, 148.7, 147.9, 141.8, 137.1, 132.2, 130.1, 129.1, 129.0, 128.3, 127.7, 127.1, 124.0, 116.6, 114.8, 59.6, 56.4, 38.8, 34.9, 20.2 ppm. ESI-RMS: m/z Calcd for C : , found exo-5c Cl 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.27 (d, J = 8.4z, 2), 7.64 (d, J = 8.8z, 2), (m, 3), 7.08 (d, J = 1.2z, 2), 7.04 (m, 1), 6.59 (d, J = 8.4z, 1), 6.34 (d, J = 2.4z, 1), 4.98 (d, J = 5.6z, 1), 4.37 (d, J = 9.2z, 1), 4,28 (s, 1), (m, 1), 2.74 (dd, J = 7.6, 16.8z, 1), 2.35 (dd, J = 2.0, 16.8z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.0, 148.1, 147.9, 142.7, 136.6, 131.4, 129.5, 129.4, 128.9, 128.2, 128.1, 124.1, 122.5, 117.9, 116.1, 59.1, 56.2, 38.5, 34.7 ppm. ESI-RMS: m/z Calcd for C Cl+ + : , found exo-5d C White solid, mp 234 ; 1 MR (400 Mz, CDCl 3 ) δ: 7.70 (d, J = 8.4z, 2), 7.58 (d, J = 8.4z, 2), (m, 3), (m, 3), 6.64 (d, J = 7.6z, 1), (m, 2), 5.03 (d, J = 5.2z, 1), 4.33 (d, J = 14.8z, 1), 4.25 (s, 1), (m, 1), 2.72 (dd, J = 7.2, 16.4z, 1), 2.33 (dd, J = 2.0, 16.4z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.3, 146.5, 144.3, 137.0, 132.7, 131.9, 129.4, 129.2, 128.9, 128.2, 127.8, 117.9, 116.5, 114.8, 112.4, 59.6, 56.4, 38.7, 34.9 ppm. ESI-RMS: m/z Calcd for C : , found endo-5d C 5

6 White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.72 (d, J = 8.0z, 2), 7.59 (d, J = 8.0z, 2), 7.43 (t, J = 7.6z, 2), 7.32 (dd, J = 7.6, 24.4z, 1), (m, 1), 6.71 (d, J = 7.6z, 1), (m, 2), 5.64 (d, J = 8.0z, 1), 4.69 (s, 1), 3.92 (s, 1), 3.22 (dd, J = 8.4z, 1), 3.08 (dd, J = 11.6, 16z, 1), 2.03 (dd, J = 7.6, 16z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 172.4, 145.8, 144.3, 138.2, 132.7, 129.3, 128.8, 127.3, 126.4, 125.6, 120.8, 119.5, 118.3, 116.2, 112.2, 60.0, 57.7, 40.7, 30.6 ppm. ESI-RMS: m/z Calcd for C : , found exo-5e C 3 C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.68 (d, J = 8.0z, 2), 7.58 (d, J = 8.4z, 2), (m, 3), 7.05 (d, J = 7.2z, 1), 6.88 (d, J = 8.0z, 1), 6.55 (d, J = 8.4z, 1), 6.15 (s, 1), 4.98 (d, J = 5.6z, 1), 4.28 (d, J = 9.2z, 1), 4.14 (s, 1), (m, 1), 2.71 (dd, J = 7.2, 16.4z, 1), 2.33 (dd, J = 2.0, 16.8z, 1), 1.94 (s, 3) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.4, 146.7, 141.9, 137.0, 132.6, 132.2, 130.1, 129.0, 128.8, 128.3, 127.7, 127.0, 118.3, 116.5, 114.7, 112.3, 59.7, 56.6, 38.7, 34.9, 21.0 ppm. ESI-RMS: m/z Calcd for C : , found exo-5f Cl C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.58 (d, J = 8.0z, 2), 7.46 (t, J = 8.0z, 2), 7.23 (d, J = 8.4z, 2), 7.04 (dd, J = 2.0, 8.4z, 1), 6.65 (d, J = 8.4z, 1), 6.49 (d, J = 1.2z, 1), 5.55 (d, J = 8.0z, 1), 4.66 (d, J = 2.8z, 1), 4.00 (s, 1), (m, 1), 3.03 (dd, J = 12.0, 16.4z, 1), 2.03 (dd, J = 8.4, 16.4z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 172.2, 145.4, 142.9, 137.7, 132.8, 129.5, 129.0, 128.8, 127.2, 126.9, 125.6, 124.0, 122.1, 118.2, 117.4, 112.3, 59.7, 57.6, 40.3, 30.3 ppm. ESI-RMS: m/z Calcd for C Cl+ + : , found exo-5g 6

7 White solid, mp 227 ; 1 MR (400 Mz, CDCl 3 ) δ: (m, 9), (m, 1), 7.06 (dt, J =1.6, 8.4z, 1),6.68 (d, J = 7.6z, 1), 6.58 (d, J =7.2z, 1),6.50 (dt, J = 0.8, 2.8z, 1), 5.64 (d, J = 7.6z, 1),4.62 (d, J = 2.4z, 1), 3.93(s, 1), (m, 2), 2.10 (dd, J =6.8, 15.6z, 1), ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.1, 145.2, 140.5, 138.4, 129.2, 129.2, 128.8, 128.6, 125.1, 126.4, 126.2, 125.6, 120.9, 118.8, 115.6, 60.2, 57.9, 41.1, 30.8 ppm. ESI-RMS: m/z Calcd for C : , found exo-5h 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.24 (d, J = 8.8z, 2), 7.57 (d, J = 8.4z, 2), 7.39 (t, J = 7.2z, 2), (m, 3), (m, 2), (m, 1), 6.77 (d, J = 8.0z, 1), 5.26 (d, J = 15.6z, 1), 4.76 (d, J = 8.8z, 1), 4.52 (d, J = 2.8z, 1), 3.95 (d, J = 15.6z, 1), 3.89 (s, 1), (m, 1), 2.98 (dd, J = 10.4, 16.0z, 1), 1.96 (dd, J = 8.4, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.4, 147.7, 147.6, 146.1, 136.0, 130.1, 138.9, 128.7, 127.8, 127.6, 127.3, 124.0, 121.4, 119.8, 116.7, 58.7, 55.8, 44.0, 40.7, 29.4 ppm. ESI-RMS: m/z Calcd for C : , found exo-5i C 3 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.23 (d, J = 8.8z, 2), 7.56 (d, J = 8.8z, 2), 7.39 (t, J = 6.8z, 2), 7.27 (d, J = 12.0z, 2), 6.97 (s, 1), 6.96 (d, J = 8.0z, 1), 6.67 (d, J = 8.0z, 1), 5.21 (d, J = 15.6z, 1), 4.73 (d, J = 8.4z, 1), 4,48 (d, J = 2.8z, 1), 3.99 (d, J = 15.6z, 1), 3.79 (s, 1), (m, 1), 2.97 (dd, J = 10.4, 16.0z, 1), 2,27 (s, 3), 1.94 (dd, J = 8.4, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.5, 147.9, 147.6, 143.6, 136.2, 130.5, 129.4, 129.0, 128.8, 127.8, 127.5, 127.3, 124.0, 121.2, 116.8, 58.9, 56.1, 44.2, 40.7, 29.4, 20.7 ppm. ESI-RMS: m/z Calcd for C : 7

8 , found exo-5j Cl 2 Yellow solid, mp 243 ; 1 MR (400 Mz, CDCl 3 ) δ: 8.25 (d, J = 8.8z, 2), 7.56 (d, J = 8.2z, 2), 7.41 (t, J = 7.6z, 2), 7.28 (d, J = 7.2z, 3), 7.15 (d, J = 2.4z, 1), 7.11 (dd, J = 2.4, 8.8z, 1), 6.70 (d, J = 8.4z, 1), 5.26 (d, J = 16.0z, 1), 4,71 (d, J = 8.8z, 1), 4,50 (d, J = 2.8z, 1), 3.94 (d, J = 15.2z, 1), 3.93 (s, 1), (m, 1), 2.93 (dd, J = 10.4, 16.4z, 1), 1.97 (dd, J = 8.8, 16.4z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.3, 147.7, 147.2, 144.6, 135.7, 129.8, 129.0, 128.7, 127.8, 127.3, 124.4, 124.1, 122.7, 117.9, 58.6, 55.6, 44.2, 40.4, 29.3 ppm. ESI-RMS: m/z Calcd for C Cl+ + : , found exo-5k C White solid, mp 240 ; 1 MR (400 Mz, CDCl 3 ) δ: 7.66 (d, J = 8.4z, 2), 7.49 (d, J = 8.4z, 2), 7.38 (t, J = 7.2z, 2), 7.27 (t, J = 6.8z, 3), (m, 2), 6.84 (t, J = 6.8z, 1), 6,75 (d, J = 7.6z, 1), 4.74 (d, J = 8.4z, 1), 4.45 (d, J = 2.8z, 1), 3.93 (d, J = 15.6z, 1), 3.91 (s, 1), 3.04 (m, 1), 2.95 (dd, J = 10.4, 16.0z, 1), 1.93 (dd, J = 8.4, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.4, 146.2, 145.7, 136.0, 132.6, 130.0, 128.8, 128.7, 127.8, 127.6, 127.2, 121.3, 119.7, 118.4, 116.7, 111.9, 58.8, 55.8, 43.9, 40.7, 29.4 ppm. ESI-RMS: m/z Calcd for C : , found exo-5l C 3 C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.65 (d, J = 8.0z, 2), 7.49 (d, J = 8.0z, 2), 7.38 (t, J = 7.2z, 2), 7.26 (d, J = 8.4z, 3), 6.94 (d, J = 8.0z, 1), 6.95 (s, 1), 6.80 (d, J = 7.6z, 1), 5.20 (d, J = 15.6z, 1), 4.71 (d, J = 4,4z, 1), 4.41 (d, J = 2.4z, 1), 3.97 (d, J = 15.6z, 1), 3.79 (s, 1), (m, 1), 2.94 (dd, J = 10.4, 8

9 16.0z, 1), 2.26 (s, 3), 1.91 (dd, J = 8.0, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 178.6, 145.9, 143.7, 136.1, 132.5, 130.5, 129.3, 128.9, 128.8, 127.7, 127.5, 127.2, 121.1, 118.3, 116.6, 111.8, 59.0, 56.1, 44.1, 43.7, 40.6, 29.3, 20.6 ppm. ESI-RMS: m/z Calcd for C : , found exo-5m C 3 C 3 White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.39 (d, J = 6.8z, 2), , (m, 5), 6.91 (t, J = 8.8z, 4), 6.61 (d, J = 8.0z, 1), 5.22 (d, J = 16.0z, 1), 4.68 (d, J = 8.8z, 1), 4.30 (d, J = 2.0z, 1), 3.98 (d, J = 15.6z, 1), 3.81 (s, 3), 3.70 (s, 1), (m, 2), 2.26 (s, 3), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ:174.4, 159.2, 144.8, 136.4, 132.6, 130.5, 129.1, 128.8, 128.2, 127.8, 127.5, 127.4, 121.3, 116.3, 114.1, 58.8, 56.4, 55.3, 44.1, 41.2, 29.6, 20.6 ppm. ESI-RMS: m/z Calcd for C : , found exo-5n White solid, mp 238 ; 1 MR (400 Mz, CDCl 3 ): δ: (m, 6), (m, 4), (M, 2),6.82 (t, J = 7.2z, 1), 6.72 (d, J =8.0z, 1),5.28 (d, J = 15.6, 1),4.73 (d, J = 8.0z, 1),4.41 (d, J = 2.0z, 1), 3.94(d, J = 15.6, 1), 3.84 (s, 1), 3.07 (dd, J = 10.4, 20.4z, 2), 2.03 (dd, J =13.2, 20.8z, 1), ppm. 13 C MR (100 Mz, CDCl 3 ) δ:174.1, 147.1, 140.4, 131.2, 130.1, 128.8, 128.8, 128.5, 127.9, 127.8, 127.5, 126.4, 121.5, 119.1, 116.4, 59.1, 56.0, 43.8, 41.0, 29.4 ppm. ESI-RMS: m/z Calcd for C : , found exo-5o C 3 C MR (400 Mz, CDCl 3 ) δ: 8.23 (d, J = 8.8z, 2), 7.61 (d, J = 8.8z, 2), 7.05 (s, 1), 9

10 7.02 (d, J = 8.4z, 1), 6.61 (d, J = 8.0z, 1), 4.52 (d, J = 5.2z, 1), 4.13 (s, 1), 4.07 (d, J = 10.4z, 1), 2.87 (s, 3), (m, 1), 2.46 (dd, J = 7.2, 8.4z, 1), 2.31 (s, 3), 2.04 (d, J = 16.8z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.0, 148.4, 148.0, 142.5, 132.1, 130.5, 129.2, 127.4, 123.9, 115.4, 115.3, 58.3, 56.4, 37.9, 34.3, 27.6, 20.4 ppm. ESI-RMS: m/z Calcd for C : , found endo-5o C 3 C MR (400 Mz, CDCl 3 ) δ: 8.25 (t, J = 4.4z, 2), 7.58 (d, J = 8.8z, 2), 7.08 (s, 1), 6.98 (d, J = 8.4z, 1), 6.68 (d, J = 8.0z, 1), 4.79 (d, J = 8.8z, 1), 4.56 (d, J = 2.8z, 1), 3.78 (s, 1), (m, 1), 2.95 (s, 1), (m, 1), 2,29 (s, 1), 1.83 (dd, J = 9.2, 16.8z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.1, 147.9, 147.6, 143.4, 130.1, 129.5, 129.1, 127.3, 124.0, 121.0, 116.7, 60.3, 58.7, 40.6, 29.3, 29.2, 20.7 ppm. ESI-RMS: m/z Calcd for C : , found endo-6a 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.22 (d, J = 8.8z, 2), 7.53 (d, J = 8.4z, 2), (m, 5), (m, 2), 6.80 (t, J = 7.2z, 2), 6.65 (dd, J = 1.2, 8.0z, 1), 5,88 (d, J = 14.8z, 1), 4.91 (d, J = 3.2z, 1), 4.85 (d, J = 4.0z, 1), 4.08 (d, J = 14.8z, 1), 4.05 (s, 1), (m, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.8, 148.3, 147.6, 142.7, 137.3, 128.8, 128.7, 128.0, 127.7, 127.4, 126.2, 123.8, 120.4, 119.0, 114.5, 58.2, 57.5, 51.6, 38.4, 29.9, 16.9 ppm. ESI-RMS: m/z Calcd for C : , found exo-6a 2 10

11 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.05 (d, J = 8.8z, 2), 7.28 (d, J = 8.8z, 2), 7.26 (s, 1), (m, 4), (m, 2), 6.75 (t, J = 7.2z, 1), 6.63 (d, J = 8.0z, 1), 5.52 (d, J = 14.4z, 1), 4.35 (s, 1), 4.07 (d, J = 3.6z, 1), 3.41 (d, J = 14.4z, 1), (m, 1), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.6, 151.4, 147.2, 142.2, 136.8, 128.9, 128.3, 128.0, 127.2, 127.1, 126.7, 123.7, 118.8, 117.9, 113.4, 57.3, 52.0, 49.9, 38.4, 29.8, 22.4 ppm. ESI-RMS: m/z Calcd for C : , found endo-6b 3 C 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.21 (d, J = 8.8z, 2), 7.52 (d, J = 8.4z, 2), (m, 5), 6.94 (d, J = 8.0z, 1), 6.90 (s, 1), 6.56 (d, J = 8.0z, 1), 5.83 (d, J = 14.4z, 1), (m, 2), 4.13 (d, J = 14.8z, 1), 3.96 (s, 1), (m, 2), 2.31 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.0, 148.5, 147.5, 140.3, 137.4, 129.2, 128.7, 128.4, 128.0, 127.7, 127.4, 126.5, 123.8, 120.4, 114.7, 58.2, 57.7, 51.8, 38.6, 29.9, 20.6, 16.9 ppm. ESI-RMS: m/z Calcd for C : , found exo-6b 3 C 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.03 (d, J = 8.8z, 2), 7.28 (d, J = 8.2z, 2), (m, 3), 6.97 (m, 3), 6.82 (s, 1), 6.55 (d, J = 8.0z, 1), 5.58 (d, J = 14.4z, 1), 4.34 (t, J = 3.2z, 1), 4.25 (t, J = 3.2z, 1), 4.03 (d, J = 14.4z, 1), 3.92 (d, J = 14.4z, 1), (m, 2), 2.24 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.7, 151.7, 147.1, 139.8, 136.9, 129.5, 128.2, 128.0, 127.3, 127.2, 127.2, 126.7, 123.7, 118.9, 113.5, 57.5, 52.0, 50.0, 38.6, 29.8, 22.5, 20.5 ppm. ESI-RMS: m/z Calcd for C : , found endo-6c 11

12 C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.65 (d, J = 8.4z, 2), 7.46 (d, J = 8.4z, 2), (m, 5), (m, 2), 7.78 (t, J = 8.0z, 1), 6.79 (dd, J = 0.8, 8.4z, 1), 5.87 (d, J = 14.8z, 1), 4.86 (d, J = 14.8z, 1), (m, 1), 4.05 (s, 1), 2.32 (t, J = 6.4z, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.8, 146.3, 142.7, 137.2, 132.4, 128.7, 128.6, 128.0, 127.6, 127.3, 126.1, 120.3, 118.8, 118.4, 114.5, 111.8, 58.3, 57.6, 51.6, 38.3, 29.9, 16.9 ppm. ESI-RMS: m/z Calcd for C : , found exo-6c C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.50 (d, J = 8.4z, 2), 7.24 (d, J = 8.0z, 2), (m, 4), 7.05 (m, J = 8.0z, 1), 6.97 (d, J = 6.8z, 2), 6.76 (m, 1), 6.61 (d, J = 8.0z, 1), 5.54 (d, J = 14.4z, 1), 4.27 (t, J = 8.8z, 1), 4.28 (s, 1), 4.07 (d, J = 4.0z, 1), 3.95 (d, J = 14.8z, 1), (m, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.8, 149.4, 142.3, 136.7, 132.2, 128.9, 128.3, 127.9, 127.3, 127.0, 126.6, 118.7, 118.5, 117.7, 113.4, 111.1, 57.4, 52.1, 49.8, 38.3, 29.7, 22.4 ppm. ESI-RMS: m/z Calcd for C : , found endo-6d 3 C C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.64 (d, J = 8.4z, 2 ) 7.46 (d, J = 8.4z, 2), (m, 5), 6.93 (d, J = 8.0z, 1), 6.89 (s, 1), 6.54 (d, J = 8.4z, 1), 5,82 (d, J = 14.4z, 1), 4.81 (t, J = 5.6z, 1), 4.12 (d, J = 14.8z, 1), 3.90 (s, 1), 2.31 (t, J = 5.6z, 2), 2.24 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C 12

13 MR (100 Mz, CDCl 3 ) δ: 171.1, 146.5, 140.3, 137.3, 132.3, 129.2, 128.7, 128.0, 127.7, 127.6, 127.3, 126.5, 120.4, 114.6, 111.7, 58.4, 57.7, 51.8, 35.5, 29.9, 20.6, 16.8 ppm. ESI-RMS: m/z Calcd for C : , found exo-6d 3 C C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.36 (d, J = 6.8z, 2), 7.23 (d, J = 8.4z, 2), (m, 3), (m, 3), 6.82 (s, 1), 6.53 (d, J = 8.0z, 1), 5.57 (d, J = 14.8z, 1), 4.27 (s, 1), 4.16 (s, 1), 4.04 (d, J = 8.0z, 1), 3.93 (d, J = 14.4z, 1), (m, 2), 2.24 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.8, 149.7, 139.9, 136.9, 132.3, 129.5, 128.3, 128.0, 127.4, 127.3, 127.1, 126.6, 118.9, 118.5, 113.5, 111.2, 57.6, 52.2, 50.0, 38.5, 29.9, 22.5, 20.5 ppm ESI-RMS: m/z Calcd for C : , found endo-6e White solid, mp 228 ; 1 MR (400 Mz, CDCl 3 ) δ: (m, 3), (m, 6), 6.98 (d, J = 6.4z, 3), 6.68 (t, J = 7.6z, 1), 6.55 (d, J = 8.0z, 1), 5.35 (d, J = 14.8z, 1), 4.34 (d, J = 3.2z, 1), 4.25 (s, 1), 4.22 (d, J = 5.2z, 1), 4.06(d, J = 14.8z, 1),, (m, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.1, 143.4, 143.3, 137.3, 128.9, 128.5, 128.2, 128.1, 127.7, 127.5, 126.9, 126.2, 118.4, 116.9, 113.3, 57.3, 53.8, 49.2, 38.4, 29.9, 22.7 ppm. ESI-RMS: m/z Calcd for C : , found exo-6e 13

14 White solid, mp 235 ; 1 MR (400 Mz, CDCl 3 ) δ: (m, 10), 7.10 (t, J = 8.0z, 2), 6.73 (t, J = 7.2z, 1), 6.59 (d, J = 7.6z, 1), 5.86 (d, J = 12.8z, 1), 4.82 (d, J = 4.0z, 1), 4.79 (d, J = 2.8z, 1), 4.07 (d, J = 12.8z, 1), 4.07 (s, 1), (m, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.2, 143.4, 140.7, 137.3, 128.7, 128.5, 128.4, 127.8, 127.8, 127.5, 126.5, 126.1, 120.1, 117.9, 113.9, 58.4, 57.8, 51.6, 38.3, 30.07, 16.9 ppm ESI-RMS: m/z Calcd for C : , found endo-6f 3 C C 3 White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: , (m, 3), 7.09 (d, J = 8.8z, 2), (m, 2), 6.92 (d, J = 9.6z, 1), 6.78 (d, J = 8.8z, 2), 6.72 (s, 1), 6.46 (d, J = 8.0z, 1), 5.37 (d, J = 14.8z 1), 4.32 (d, J = 4.0z, 1), 4.14 (d, J = 6.0z, 1), 4.06 (d, J = 14.4z, 1),.4.05 (s,1), 3.78 (s, 3), (m, 2), 2.20 (s, 3), 2.17(s, 1), (m, 1), (m,1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.2, , 141.1, 137.6, 135.7, 129.5, 128.6, 128.2, 127.8, 127.3, 126.9, 126.1, 118.5, 113.9, 113.4, 57.0, 55.2, 54.1, 49.2, 38.8, 30.0, 22.5, 20.4 ppm. ESI-RMS: m/z Calcd for C : , found exo-6f 3 C C 3 White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: , (m, 4), (m, 3), (m, 4), 6.49 (d, J = 8.0z, 1), 5.82 (d, J = 14.4z, 1), 4.80 (d, J = 4.4z, 1), 4.70 (d, J = 2.8z, 1), 4.12 (d, J = 14.4z, 1), 3.86 (s, 1), 3.80 (s, 3), (dt, J = 4.4, 7.6z 2), 2.14 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.4, 159.2, 141.1, 137.5, 132.9, 129.0, 128.7, 128.0, 127.6, 127.5, 127.2, 126.6, 120.3,114.1, 113.4, 58.0, 58.0, 55.3, 51.8, 38.8, 30.2, 20.6, 17.0 ppm. ESI-RMS: m/z Calcd for C : , found

15 1 MR and 13 C MR Spectra endo-5a 15

16 exo-5a 16

17 exo-5b 17

18 exo-5c 18

19 endo-5d 19

20 exo-5d 20

21 exo-5e 21

22 exo-5f 22

23 exo-5g 23

24 exo-5h 24

25 exo-5i 25

26 exo-5j 26

27 exo-5k 27

28 exo-5l 28

29 exo-5m 29

30 exo-5n 30

31 endo-5o 31

32 exo-5o 32

33 endo-6a 33

34 exo-6a 34

35 endo-6b 35

36 exo-6b 36

37 endo-6c 37

38 exo-6c 38

39 endo-6d 39

40 exo-6d 40

41 endo-6e 41

42 exo-6e 42

43 endo-6f 43

44 exo-6f 44

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