Total syntheses of cannabicyclol, clusiacyclol A and B, iso-eriobrucinol A and B, and eriobrucinol

Organic Letters

Volumn 15, Issue 12, 2013, Pages 3130-3133

  Yeom, Hyun Suk ^a   Li, Hui ^b   Tang, Yu ^b   Hsung, Richard P ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b TIANJIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; CANNABICYCLOL; CANNABINOID; CHROMAN DERIVATIVE; CLUSIACYCLOL A; CLUSIACYCLOL B;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; CANNABINOIDS; CHROMANS; CYCLOADDITION REACTION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84879367914     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401335u     Document Type: Article

References (85)

1. Kurdyumov, A. V.; Hsung, R. P. J. Am. Chem. Soc. 2006, 128, 6272
2. Stadler, P. A.; Eschenmoser, A.; Schinz, H.; Stork, G. Helv. Chim. Acta 1957, 40, 2191
3. Johnson, W. S. Acc. Chem. Res. 1968, 1, 1
4. Roll, D. M.; Manning, J. K.; Carter, G. T. J. Antibiot. 1998, 51, 635
5. For fermentation studies, see: Abbanat, D. A.; Singh, M. P; Greenstein, M. J. Antibiot. 1998, 51, 708
6. Tsujimori, H.; Bando, M.; Mori, K. Eur. J. Org. Chem. 2000, 297
7. Tsujimori, H.; Mori, K. Biosci. Biotechnol. Biochem. 2000, 64, 1410
8. For a recent review on biomimetic synthesis, see: Bulger, P. G.; Bagal, S. K.; Marquez, R. Nat. Prod. Rep. 2008, 25, 254
9. Yoder, R. A.; Johnston, J. N. Chem. Rev. 2005, 105, 4730
10. Beaudry, C. M.; Malerich, J. P.; Trauner, D. Chem. Rev. 2005, 105, 4757
11. Pindur, U.; Schneider, G. H. Chem. Soc. Rev. 1994, 409
12. For a leading reference, see: Thulasiram, H. V.; Erickson, H. K.; Poulter, C. D. Science 2007, 316, 73
13. Gassman, P. G.; Chavan, S. P.; Fertel, L. B. Tetrahedron Lett. 1990, 31, 6489
14. Gassman, P. G.; Lottes, A. C. Tetrahedron Lett. 1992, 33, 157
15. Harmata, M.; Rashatasakhon, P. Tetrahedron 2003, 59, 2371
16. Harmata, M. Tetrahedron 1997, 53, 6235
17. For a leading review on thermally driven [2 + 2] cycloadditions, see: Baldwin, J. E.; Trost, B. M.; Fleming, I.; Pattenden, G. Comprehensive Organic Synthesis; Pergamon Press: New York, 1991; p 63.
18. Ko, C.; Feltenberger, J. B.; Ghosh, S. K.; Hsung, R. P. Org. Lett. 2008, 10, 1971
19. Feltenberger, J. B.; Ko, C.; Deng, J.; Ghosh, S. K.; Hsung, R. P. Heterocycles 2012, 84, 843
20. Deng, J.; Hsung, R. P.; Ko, C. Org. Lett. 2012, 14, 5562
21. For a leading review, see: Shen, H. C. Tetrahedron 2009, 65, 3931
22. Crombie, L.; Redshaw, S. D.; Black, D. A.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1983, 1411
23. Crombie, L.; Ponsford, R. J. Chem. Soc. C 1971, 796
24. Crombie, L.; Ponsford, R.; Shani, A.; Yagnitinsky, B.; Mechoulam, R. Tetrahedron Lett. 1968, 9, 5771
25. For basic conditions to promote cyclobutane formation and total syntheses of clusiacyclol A and B, see: Mondal, M.; Puranik, V. G.; Argade, N. P. J. Org. Chem. 2007, 72, 2068
26. For cyclobutane formation using pyridine, see: Montero, J. L.; Winternitz, F. Tetrahedron 1973, 29, 1243
27. Crombie, L.; Ponsford, R. Chem. Commun. [London] 1968, 894
28. Crombie, L.; Crombie, W. M. L. Phytochemistry 1975, 14, 213
29. Kane, V. V.; Razdan, R. K. J. Am. Chem. Soc. 1968, 90, 6551
30. 2O, see: Yagen, B.; Mechoulam, R. Tetrahedron Lett. 1969, 10, 5353
31. For a cationic ene-cyclization mechanism, see: Kane, V. V. Tetrahedron Lett. 1971, 12, 4101
32. For isolation, see: Kashiwada, Y.; Yamazaki, K.; Ikeshiro, Y.; Yamagishi, T.; Fujioka, T.; Mihashi, K.; Mizuki, K.; Cosentino, L. M.; Fowke, K.; Morris-Natschke, S. L.; Lee, K.-H. Tetrahedron 2001, 57, 1559
33. Kurdyumov, A. V.; Hsung, R. P.; Ihlen, K.; Wang, J. Org. Lett. 2003, 5, 3935
34. Kang, Y.; Mei, Y.; Du, Y.; Jin, Z. Org. Lett. 2003, 5, 4481
35. Hu, H.; Harrison, T. J.; Wilson, P. D. J. Org. Chem. 2004, 69, 3782
36. Harrity, J. P. A.; Provoost, O. Org. Biomol. Chem. 2005, 3, 1349
37. Hsung, R. P.; Kurdyumov, A. V.; Sydorenko, N. Eur. J. Org. Chem. 2005, 1, 23
38. Hsung, R. P.; Cole, K. P. Strategies and Tactics in Organic Synthesis; Pergamon Press: Oxford, U.K., 2004; p 41.
39. Fotiadou, A. D.; Zografos, A. L. Org. Lett. 2012, 14, 5664
40. Hu, J.; Dong, W.; Wu, X.-Y.; Tong, X. Org. Lett. 2012, 14, 5530
41. dos Samntos, W. H.; da Silva-Filho, L. C. Synthesis 2012, 3361
42. Lee, Y. R.; Pandit, R. P. Synthesis 2012, 2910
43. Parker, K. A.; Thomas L. Mindt, T. L. Tetrahedron 2011, 67, 9779
44. Jung, E. J.; Park, B. H.; Lee, Y. R. Green Chem. 2010, 12, 2003
45. Yamamoto, Y.; Itonaga, K. Org. Lett. 2009, 11, 717
46. Sagar, R.; Park, J.; Koh, M.; Park, S. B. J. Org. Chem. 2009, 74, 2171
47. Hubert, C.; Moreau, J.; Batany, J.; Duboc, A.; Hurvois, J.-P.; Renaud, J.-L. Adv. Synth. Catal. 2008, 350, 40
48. Brioche, J. C. R.; Goodenough, K. M.; Whatrup, D. J.; Harrity, J. P. A. J. Org. Chem. 2008, 73, 1946
49. Song, L.; Yao, H.; Zhu, L.; Tong, R. Org. Lett. 2013, 15, 6
50. Li, H.; Tang, Y.; Hsung, R. P. Tetrahedron Lett. 2012, 53, 6138
51. Buchanan, G. S.; Cole, K. P.; Tang, Y.; Hsung, R. P. J. Org. Chem. 2011, 76, 7027
52. Buchanan, G. S.; Cole, K. P.; Li, G.; Tang, Y.; You, L.; Hsung, R. P. Tetrahedron 2011, 67, 10105
53. Yamashita, S.; Iso, K.; Kitajima, K.; Himura, M.; Hirama, M. J. Org. Chem. 2011, 76, 2408
54. Wang, X.; Lee, Y. R. Tetrahedron 2011, 67, 9179
55. Hosokawa, S.; Matsushita, K.; Tokimatsu, S.; Toriumi, T.; Suzuki, Y.; Tatsuta, K. Tetrahedron Lett. 2010, 51, 5532
56. Tang, Y.; Cole, K. P.; Buchanan, G. S.; Li, G.; Hsung, R. P. Org. Lett. 2009, 11, 1591
57. Wang, X.; Lee, Y. R. Tetrahedron 2009, 65, 10125
58. Jeso, V.; Nicolaou, K. C. Tetrahedron Lett. 2009, 50, 1161
59. Lee, Y. R.; Li, X.; Kim, J. H. J. Org. Chem. 2008, 73, 4313
60. Yamashita, S.; Iso, K.; Hirama, M. Org. Lett. 2008, 10, 3413
61. Lee, Y. R.; Kim, J. H.; Yong, C. S.; Im, J. S.; Lyoo, W. S. Bull. Korean Chem. Soc. 2008, 29, 515
62. Tietze, L. F. Chem. Rev. 1996, 96, 115
63. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. 1993, 32, 131
64. Tietze, L. F. J. Heterocycl. Chem. 1990, 27, 47
65. For isolations of clusiacyclol A and B: Gonzalez, J. G.; Olivares, E. M.; Monache, F. D. Phytochemistry 1995, 38, 485
66. Jefferies, P. R.; Worth, G. K. Tetrahedron 1973, 29, 903
67. Bukuru, J.; Van, T. N.; Puyvelde, L. V.; He, W.; De Kimpe, N. Tetrahedron 2003, 59, 5905
68. For additional eriobrucinol data, see: Rashid, M. A.; Armstrong, J. A.; Gray, A. I.; Waterman, P. G. Phytochemistry 1992, 31, 3583
69. Crombie, L.; Redshaw, S. D.; Black, D. A.; Whiting, D. A. J. Chem. Soc., Chem. Commun. 1979, 628
70. Claussen, U.; von Spulak, F.; Korte, F. Tetrahedron 1968, 24, 1021
71. Begley, M. J.; Clarke, D. G.; Crombie, L.; Whiting, D. A. J. Chem. Soc. D 1970, 1547
72. Gaoni, Y.; Mechoulam, R. J. Am. Chem. Soc. 1971, 93, 217
73. Boeren, E. G.; Elsohly, M. A.; Turner, C. E. J. Heterocycl. Chem. 1978, 15, 699
74. Turner, C. E.; Elsohly, M. A.; Boeren, E. G. J. Nat. Prod. 1980, 43, 169
75. Kane, V. V.; Martin, A. R.; Peters, J. A. J. Org. Chem. 1984, 49, 1793
76. Hsung, R. P.; Shen, H. C.; Douglas, C. J.; Morgan, C. D.; Degen, S. J.; Yao, L. J. J. Org. Chem. 1999, 64, 690
77. Shen, H. C.; Wang, J.; Cole, K. P.; McLaughlin, M. J.; Morgan, C. D.; Douglas, C. J.; Hsung, R. P.; Coverdale, H. A.; Gerasyuto, A. I.; Hahn, J. M.; Liu, J.; Wei, L.-L.; Sklenicka, H. M.; Zehnder, L. R.; Zificsak, C. A. J. Org. Chem. 2003, 68, 1729
78. For a related condensation using ethylene diamine acetate salt that led to cannabichromene: Lee, Y. R.; Wang, X. Bull. Korean Chem. Soc. 2005, 26, 1933
79. Mechoulam, R.; Yapnitinsky, B.; Y. Gaoni, Y. J. Am. Chem. Soc. 1968, 90, 2420
80. 13C NMR characterization data were incomplete and there was no stereochemistry assigned therein. See: Eisohly, H. N.; Turner, C. E.; Clark, A. M.; Eisohly, M. A. J. Pharm. Sci. 1982, 71, 1319
81. For a related condensation that led to tetrahydrocannabinol, see: Taylor, E. C.; Lenard, K.; Shvo, Y. J. Am. Chem. Soc. 1965, 87, 367
82. For the citran/cyclol mechanism, see: Begley, M. J.; Crombie, L.; King, R. W.; Slack, D. A.; Whiting, D. A. J. Chem. Soc., Chem. Commun. 1977, 2393
83. For consideration of a hetero-Diels-Alder pathway, see: Crombie, L.; Redshaw, S. D.; Whiting, D. A. J. Chem. Soc., Chem. Commun. 1979, 630
84. Zehnder, L. R.; Dahl, J. W.; Hsung, R. P. Tetrahedron Lett. 2000, 41, 1901
85. Melliou, E.; Magiatis, P.; Mitaku, S.; Skaltsounis, A.-L.; Chinou, E.; Chinou, I. J. Nat. Prod. 2005, 68, 78