Total Syntheses of (±)-Isosteviol and (±)-Beyer-15-ene-3β,19-diol by Manganese(III)-Based Oxidative Quadruple Free-Radical Cyclization

Journal of Organic Chemistry

Volumn 63, Issue 22, 1998, Pages 7945-7952

  Snider, Barry B ^a   Kiselgof, Jane Y ^a   Foxman, Bruce M ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001377167     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981238x     Document Type: Article

References (44)

1. 3 as an oxidant see: (a) Snider, B. B. Chem. Rev. 1996, 96, 339.
2. (b) Melikyan, G. G. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 49, Chapter 3.
3. (a) Snider, B. B.; Mohan, R. M.; Kates, S. A. Tetrahedron Lett. 1987, 841.
4. (b) Snider, B. B.; Dombroski, M. A. J. Org. Chem. 1987,52, 5487.
5. Dombroski, M. A.; Kates, S. A.; Snider, B. B. J. Am. Chem. Soc. 1990, 112, 2759.
6. (a) Zoretic, P. A.; Zhang, Y.; Fang, H.; Ribeiro, A. A.; Dubay, G. J. Org. Chem. 1998, 63, 1162.
7. (b) Zoretic, P. A.; Wang, M.; Zhang, Y.; Shen, Z. J. Org. Chem. 1996, 61, 1806.
8. Zoretic, P. A.; Chen, Z.; Zhang, Y.; Ribeiro, A. A. Tetrahedron Lett. 1996, 7909.
9. Zoretic, P. A.; Zhang, Y.; Ribeiro, A. A. Tetrahedron Lett. 1996, 1751.
10. (e) Zoretic, P. A.; Wang, M. Synth. Commun. 1996, 26, 2783 and references therein.
11. (f) Zoretic, P. A.; Fang, H.; Riberio, A. A. J. Org. Chem. 1998, 63, 4779.
12. For a review of diterpene synthesis see: Goldsmith, D. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1992; Vol. 8, pp 1-243.
13. (a) Mosettig, E.; Beglinger, U.; Dolder, F.; Lichti, H.; Quitt, P.; Waters, J. A. J. Am. Chem. Soc. 1963, 85, 2305.
14. (b) Mosettig, E.; Nes, W. J. Org. Chem. 1955, 20, 884.
15. Lloyd, H. A.; Fales, H. M. Tetrahedron Lett. 1967, 4891.
16. (a) Negishi, E.; Zhang, Y.; Bagheri, V. Tetrahedron Lett. 1987, 28, 5793 and references therein.
17. (b) Zhang, Y.; Wu, G.; Agnel, G.; Negishi, E. J. Am. Chem. Soc. 1990, 112, 8590.
18. Zhang, Y. Ph.D. Thesis, Purdue University, 1989.
19. (a) Takacs, J. M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 5, p 3191.
20. (b) Baker, K. V.; Brown, J. M.; Hughes, N.; Skarnulis, A. J.; Sexton, A. J. Org. Chem. 1991, 56, 698.
21. Hooz, J.; Calzada, J. G.; McMaster, D. Tetrahedron Lett. 1985, 271.
22. Duboudin, J. G.; Jousseaume, B. J. Organomet. Chem. 1979, 168, 1.
23. Corey, E. J.; Lin, S. J. Am. Chem. Soc. 1996, 118, 8765.
24. These chemical shifts are very similar to those of 3-methylenecyclooctene: Stierman, T. J.; Johnson, R. P. J. Am. Chem. Soc. 1985, 707, 3971.
25. Snider, B. B.; Merritt, J. E. Tetrahedron 1991, 47, 8663.
26. (a) Kuwajima, I.; Doi, Y. Tetrahedron Lett. 1972, 1163.
27. (b) Coates, R. M.; Ley, D. A.; Cavender, P. L. J. Org. Chem. 1978, 43, 4915.
28. Horner-Emmons reaction of aldehyde 20 with triethyl 2-phosphonopropionate yielded 84% of α,β-unsaturated ester 21 as a 1.3:1 mixture of E- and Z-isomers.
29. (a) Thomas, A. F. Swiss Patent 510,602, 1971.
30. (b) Thomas, A. F. J. Am. Chem. Soc. 1969,91,3281.
31. Thomas, A. F. Chem. Commun. 1967, 947.
32. Cookson, R. C.; Rogers, N. R. J. Chem. Soc., Perkin Trans, l 1973, 2741.
33. X-ray crystallographic data have been deposited at the Cambridge Crystallographic Data Centre.
34. Aranda, G.; Lallemand, J.-Y.; Azerad, R.; Maurs, M.; Cortes, M.; Ramirez, H.; Vernal, G. Synth. Commun. 1994, 24, 2525.
35. Ireland, R. E.; Mander, L. N. Tetrahedron Lett. 1965, 2627;
36. Mori, K.; Matsui, M. Tetrahedron Lett. 1970, 3287.
37. Shapiro, R. H. In Organic Reactions; Dauben, W. G., Ed.; Wiley: New York, 1976; Vol. 23, Chapter 3.
38. (a) Bailey, P. S. In Ozonation in Organic Chemistry; Trahanovsky, W., Ed.; Academic: New York, 1978; Vol. 1, pp 147-183.
39. (b) Bailey, P. S. Chem. Ber. 1955,88, 795.
40. Hanson, J. R. J. Chem. Soc. 1963, 5061.
41. Delgado, G.; Romo de Vivar, A.; Ortega, A.; Cardenas, J.; Schlemper, E. O. Phytochemistry 1983, 22, 1227.
42. von Carstenn-Lichterfelde, C.; Pascual, C.; Rabanal, R. M.; Rodriguez, B.; Valverde, S. Tetrahedron 1977, 33, 1989.
43. (a) Grande, M.; Morán, J.; Macías, M. J.; Mancheño, B. Phytochem. Anal. 1993, 4, 19;
44. Chem. Abstr. 1993, 118, 229498w.