Mild Generation of o-Quinone Methides. Synthesis of (-)-Hexahydrocannabinol and Dihydrocannabidiol

References and Notes

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• Data for 7: UV (EtOH) λmax: 208, 226, 275, 282 nm; IR (CHCl3): 3595, 2920, 2850, 1623, 1575, 1457, 1418, 1355, 1260, 1136, 1052, 1035, 1017 cm−1; 1H-NMR (500 MHz, CDCl3) δ: 6. 24 (s, 1H, ArH), 6. 08 (s, 1H, ArH1), 4. 58 (s, 1H, OH), 3. 03 (br d, 1H, J=12. 4 Hz, 10-Heq), 2. 42 (br m, 3H1 10a-H, aCH2), 1. 85 (br m, 2H, 8-Heq, 7-Heq), 1. 57 (m, 9H, bCH2), 1. 45 (“t”, 1H, J=10. 4Hz, 6a-H), 1. 36 (s, 3H, 6-Me), 1. 10 (m, 7-Hax), 1. 07 (s, 3H, 6-Me), 0. 94 (d, 3H, J=6. 1 Hz, 9-Me), 0. 88 (t, 3H, e-Me); 13C-NMR (CDCl3) δ: 154. 93, 154. 66, 142. 53, 110. 28, 110. 03, 107. 63, 76. 97, 49. 13, 38. 98, 35. 52, 35. 40, 35. 38, 32. 83, 31. 55, 30. 55, 28. 05, 27. 71, 22. 57, 22. 52, 19. 02, 13. 99; MS: m/e 317(23), 316(100), 301(10), 273(94), 260(81), 231(26), 193(60), 149(10), 123(15), 81(12), 67(20), 55(23); Exact Mass for C21H32O2: calcd.: 316. 2405, obtained: 316. 2402
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• Data for 6: UV (EtOH) λmax: 207, 226, 273 nm; IR (CHCl3): 3600, 2915, 2845, 1625, 1589, 1455, 1425, 1250, 1260, 1114, 1010, 890 cm−1; 1H-NMR (500 MHz, CDCl3) δ: 6. 15 (s, 1H, Ar-H), 6. 08 (s, 1H, Ar-H1), 4. 66 (s, 1H, vinyl H), 4. 58, 4. 57 (s, s, 2H, 2 × OH), 4. 50 (s, 1H. vinyl H), 3. 09 (m, 1H, 3-H), 2. 86 (m, 1H, 4-H), 2. 40 (t, 2H, J=7. 7 Hz, aCH2), 1. 54 (br, overlapped, vinyl Me), 0. 92 (d, J=6. 4 Hz, 1-Me), 0. 89 (t, J=6. 8 Hz, e-Me); 13C-NMR (CDCl3) δ: 155. 27, 153. 67, 150. 20, 141. 89, 115. 54, 109. 25 (2C), 108. 22, 47. 59, 39. 41, 38. 54, 35. 24, 35. 20, 33. 29, 33. 15, 31. 56, 30. 50, 22. 51, 22. 48, 19. 57, 14. 00; MS: m/e 317(30), 316(91), 301(18), 274(32), 273(89), 260(71), 233(85), 231(54), 193(100), 123(37), 81(57), 69(85); Exact Mass for C21H23O2: calcd.: 316. 2405, obtained: 316. 2402
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