Tandem use of cobalt-mediated reactions to synthesize (+)- epoxydictymene, a diterpene containing a trans-fused 5-5 ring system

Journal of the American Chemical Society

Volumn 119, Issue 19, 1997, Pages 4353-4363

  Jamison, Timothy F ^a   Shambayati, Soroosh ^a   Crowe, William E ^a,b   Schreiber, Stuart L ^a  

^a HARVARD UNIVERSITY   (United States)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; EPOXYDICTYMENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0030991958     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970022u     Document Type: Article

References (49)

1. Enoki, N.; Furusaki, A.; Suehiro, K.; Ishida, R.; Matsumoto, T. Tetrahedron Lett. 1983, 24, 4341.
2. For a review concerning the synthesis of carbocyclic eight-membered rings, see: Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.
3. α-Funebrene: Kirtany, J. K.; Paknikar, S. K. J. Indian Chem. 1973, 11, 508.
4. Paradalianchol: Bohlmann, F.; Abraham, W. F. Phytochemistry 1979, 18, 668.
5. α-8-Hydroxypresilphiperfolene: Bohlmann, W. F.; Zdero, C.; Jakupovic, J.; Robinson, H.; King, R. M. Phytochemistry 1981, 20, 2239.
6. Chang, S.; McNally, D.; Shary-Tehrany, S.; Hickey, M. J.; Boyd, R, H. J. Am. Chem. Soc. 1970, 92, 3109.
7. Allinger, N. L.; Tribble, M. T.; Miller, M. A.; Wertz, D. H. J. Am. Chem. Soc. 1971, 93, 1637.
8. Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128.
9. Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749.
10. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289.
11. (a) For a preliminary account of this work: Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J. Am. Chem. Soc. 1994, 116, 5505.
12. (b) An alternative total synthesis of epoxydictymene appeared after submission of this work: Paquette, L. A.; Sun, L.-Q.; Friedrich, D.; Savage, P. B. Tetrahedron Lett. 1997, 38, 195.
13. Schoening, A.; Friedrichsen, W. Z. Naturforsch. 1989, 44b, 975.
14. For a review on the Pauson-Khand reaction see: Pauson, P. L. Tetrahedron 1985, 41, 5855.
15. Schore, N. E. Org. React. 1991, 40, 1.
16. Wolinsky, J.; Gibson, T.; Chan, D.; Wolf, H. Tetrahedron 1965, 21, 1247.
17. Schlosser, M. Angew. Chem., Int. Ed. Engl. 1974, 13, 701.
18. Morton, H. E.; Guindon, Y. J. Org. Chem 1985, 50, 5379.
19. Ishihara, K.; Yamamoto, H.; Heathcock, C. H. Tetrahedron Lett. 1989, 30, 1825.
20. Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485.
21. Grieco, P. A.; Jaw, J. Y.; Claremon, J. A.; Nicolaou, K. C. J. Org. Chem. 1981, 46, 1215.
22. Schreiber, S. L.; Wang, Z.; Schulte, G. Tetrahedron Lett. 1988, 29, 4085.
23. Denmark, S. E.; Willson, T. M.; Almstead, N. G. J. Am. Chem. Soc. 1989, 111, 9258.
24. Mori, I.; Ishihara, K.; Flippin, L. A.; Nozaki, K.; Yamamoto, H.; Bartlett, P. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 6107.
25. Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1991, 113, 8089.
26. Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998.
27. Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1994, 116, 7915.
28. Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233.
29. Bladon, P.; Brunner, P. L.; Eder, R. J. Organomet. Chem. 1988, 358, 845.
30. Stork, G.; Darling, S. D. J. Am. Chem. Soc. 1960, 82, 1512.
31. Stork, G.; Tsuji, J. J. Am. Chem. Soc. 1961, 83, 2783.
32. Stork, G.; Rosen, P.; Goldman, N. L. J. Am. Chem. Soc. 1961, 83, 2965.
33. Review: Caine, D. Org. React. 1976, 23, 1.
34. Markgraf, J. H.; Staley, S. W.; Allen, T. R. Synth. Commun. 1989, 19, 1471.
35. Agnel, G.; Owczarczyk, Z.; Negishi, E. Tetrahedron Lett. 1992, 33, 1543.
36. Mander, L. N.; Sethi, S. P. Tetrahedron Lett. 1983, 24, 5425.
37. Isolation and structure of ingenol, which contains an "inside-outside" bridged ring system: Zechmeister, K.; Brandl, F.; Hoppe, W.; Hecker, E.; Opferkuch, H. J.; Adolf, W. Tetrahedron Lett. 1970, 11, 4075.
38. For a review on the "inside-outside" bridged ring system: Alder, R. W. Acc. Chem. Res. 1983, 16, 321.
39. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
40. Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 2000.
41. Bailey, W. F.; Khanolkar, A. D. Tetrahedron Lett. 1990, 31, 5993.
42. Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053.
43. Review: Curran, D. P. Radical Cyclization and Sequential Radical Reactions; Curran, D. P., Ed.; Pergamon Press: New York, 1991; Vol. 4.2, pp 779-831.
44. Chatgilialoglu, C.; Griller, D.; Lesage, M. J. Org. Chem. 1988, 53, 3642.
45. Kulicke, K. J.; Giese, B. Synlett 1990, 91.
46. Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47.
47. Giese, B. Angew, Chem., Int. Ed. Engl. 1983, 22, 753.
48. Ohsawa, T.; Kobayashi, T.; Mizuguchi, Y.; Saitoh, T.; Oishi, T. Tetrahedron Lett. 1985, 26, 6103.
49. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.