A new approach to phorbol by [4 + 3] oxyallyl cycloaddition and intramolecular Heck reaction

Organic Letters

Volumn 1, Issue 3, 1999, Pages 523-525

  Lee, Kwangho ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; PHORBOL DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALLYL COMPOUNDS; CYCLIZATION; PHORBOLS; STEREOISOMERISM;

EID: 0033549669     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990709e     Document Type: Article

References (33)

1. (a) Naturally Occurring Phorbol Esters; Evans F. J., Ed.; CRC Press Boca Raton, FL, 1986.
2. (b) Hecker, E.; Schmidt, R. Fortschr. Chem. Org. Naturst. 1974, 31, 377.
3. (c) Evans, F. J., Taylor, S. E. Fortschr. Chem. Org. Naturst. 1983, 44, 1.
4. (d) Fraga, B. M. Nat. Prod. Rep. 1992, 9, 217.
5. (a) Wender, P. A.; Kogen, H.; Lee, H. Y.; Munger, J. D., Jr.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957.
6. (b) Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956.
7. (c) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897.
8. (d) Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976.
9. For recent reviews, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
10. (b) Jeffery, T. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI: Greenwich, CT, 1996; Vol. 5.
11. (c) Overman, L. E.; Link, J. T. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; VCH: New York, 1998. For recent representative examples of the intramolecular Heck reaction to form a fused bicyclic ring system, see:
12. (d) Overman, L. E.; Ricca, D. J.; Tran, V. D. J. Am. Chem. Soc. 1997, 119, 12031.
13. (e) Jin, J.; Weinreb, S. M. J. Am. Chem. Soc. 1997, 119, 2050.
14. (f) Negishi, E.; Ma, S.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922.
15. For reviews on oxyallyls, see: (a) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
16. (b) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1.
17. (c) Mann, J. Tetrahedron 1986, 42, 4611.
18. (d) Rigby, J. H.; Pigge, F. C. Org. React. 1997, 51, 351.
19. (e) Harmata, M. Tetrahedron 1997, 53, 6235.
20. Part 10 in the series synthetic studies on [4 + 3] cycloadditions of oxyallyls For previous papers in the series, see the following references. (a) Part 9: Cho, S. Y.; Lee, J. C.; Cha, J. K. J. Org. Chem. 1999, 64, 3394.
21. (b) Part 8: Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804.
22. (c) Part 7: Cha, J. K.; Oh, J. Curr. Org. Chem. 1998, 2, 217.
23. (d) Part 6: Jin, S.; Choi, J.-R.; Oh, J.; Lee, D.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 10914.
24. Pevzner, L. M.; Ignat'ev, V. M.; Golubkov, I. M. Zh. Org. Khim. 1989, 25, 843.
25. Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Hendle, G. H.; Korfant, H.; Reiner, S.; Föhlisch, B. J. Org. Chem. 1999, 64, 3398 and references therein.
26. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
27. Cf.: Larock, R. C.; Johnson, P. L. J. Chem. Soc., Chem. Commun. 1989, 1368 and references therein.
28. (a) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954.
29. (b) Treatment of 14 bearing the β,β-dimethyl group at C5 and C10 (phorbol numbering) with t-BuLi resulted in transmetalation and elimination, but no cyclization, to afford a mixture of the corresponding terminal olefin and acetylene products, respectively: Lee, K.; Cha, J. K. Unpublished observations.
30. Wender, P. A.; McDonald, F. E. Tetrahedron Lett. 1990, 31, 3691.
31. (a) Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336.
32. (b) RajanBabu, T. V.; Nugent, W. A.; Taber, D. F.; Fagan, P. J. J. Am. Chem. Soc. 1988, 110, 7128.
33. For an excellent review on ring-opening reactions of oxabicyclic compounds, see: Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 1.