Synthetic studies on the ingenane diterpenes. Construction of an ABC tricycle exhibiting trans-intrabridgehead stereochemistry

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2265-2268

  Rigby, James H ^a   Jingdan, Hu ^a   Heeg, Mary Jane ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; INGENOL;

ARTICLE; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0032537201     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00243-3     Document Type: Article

References (24)

1. 1 (a) Hecker, E. Pure Appl. Chem. 1977, 49, 1423.
2. (b) Evans, F. J.; Taylor, S. E. Prog. Chem. Org. Nat. Prod. 1983, 44, 1.
3. 2. For discussion of the tumor-promoting activity of ingenol, see: (a) Hecker, E.; Fusening, N. E.; Kunz, W.; Marks, F.; Thielmann, H. W.; Eds. Carcinogenesis, Vol. 7, Cocarcinogenesis and Biological Effects of Tumor Promoters; Raven Press: New York, 1982.
4. (b) Sorg, B.; Schmidt, R.; Hecker, E. Carcinogenesis 1987, 8, 1.
5. 3. For recent reviews of synthetic approaches into ingenol, see: (a) Rigby, J. H.; in Studies in Natural Products Chemistry; Rahman, A.-u., Ed.; Elsevier: Amsterdam, 1993, Vol. 12 (Part H), pp. 233-74.
6. (b) Kim, S.; Winkler, J. D. Chem. Soc. Rev. 1997, 26, 387.
7. 4. Ingenol has been calculated to be 5.9 kcal/mol more strained than its epimer at C-8: Funk, R. L.; Olmstead, T. A.; Parvez, M. J. Am. Chem. Soc. 1988, 110, 3298.
8. 5. (a) Winkler, J. D.; Henegar, K. E.; Williard, P. G. J. Am. Chem. Soc. 1987, 109, 2850.
9. (b) Winkler, J. D.; Hong, B.-C.; Bahador, A.; Kazanietz, M. G.; Blumberg, P. M. Bioorg. Med. Chem. Lett. 1993, 3, 577.
10. (c) Winkler, J. D.; Henegar, K. E.; Hong, B.-C.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 4183.
11. 6. Funk, R. L.; Olmstead, T. A.; Parvez, M.; Stallman, J. B. J. Org. Chem. 1993, 58, 5873.
12. 7. Rigby, J. H.; de Sainte Claire, V.; Cuisiat, S. V.; Heeg, M. J. J. Org. Chem. 1996, 61, 7992
13. 8. Nakamura, T.; Matsui, T.; Tanino, K.; Kuwajima, I. J. Org. Chem. 1997, 62, 3032.
14. 9. (a) Rigby, J. H.; Rege, S. D.; Sandanayaka, V. P.; Kirova, M. J. Org. Chem. 1996, 61, 842.
15. (b) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am.Chem. Soc. 1993, 115, 1382.
16. 10. Munro, J. D.; Pauson, P. L. J. Chem. Soc. 1961, 3475.
17. 11. Yeh, M.-C. P.; Sheu, B.-A.; Fu, H.-W.; Tau, S.-I.; Chuang, L.-W. J. Am. Chem. Soc. 1993, 115, 5941.
18. 12. Roush, W. R.; Gillis, H. R.; Ko, A. I. J. Am. Chem. Soc. 1982, 104, 2269.
19. 13C NMR, IR) and analytical (combustion analysis and/or HRMS) data fully consistent with the assigned structure.
20. 14. (a) Foreman, M. I.; Knox, G. R.; Pauson, P. L.; Todd, K. H.; Watts, W. E. J. Chem. Soc., Perkin Trans 2 1972, 1141.
21. (b) Roth, W. R.; Grimme, W. Tetrahedron Lett. 1966, 2347.
22. 15. Rigby, J. H.; Sandanayaka, V. P. Tetrahedron Lett. 1993, 34, 935.
23. 16. Paquette, L. A.; Crouse, G. D.; Sharma, A. K. J. Am. Chem. Soc. 1980, 102, 3972.
24. 17. The authors have deposited atomic coordinates for 12 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IE2, UK.