A Novel Method for Stereospecific Generation of Either C-20 Epimer in Steroid Side Chains by Palladium-Catalyzed Hydrogenolysis of C-20 Allylic Carbonates

Journal of Organic Chemistry

Volumn 57, Issue 23, 1992, Pages 6090-6092

  Mandai, Tadakatsu ^a   Matsumoto, Takaji ^a   Kawada, Mikio ^a   Tsuji, Jiro ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

STEROID;

ARTICLE; ISOMERISM; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0026685695     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00049a004     Document Type: Article

References (29)

1. Batcho, A. D.; Berger, D. E.; Davoust, S. G.; Wovkulich, P. M.; Uskokovic, M. R. Helv. Chim. Acta 1981, 64, 1682.
2. Dauben, W. G.; Brookhart, T. J. Am. Chem. Soc., 1981, 103, 237
3. Batcho, A. D.; Berger, D. E.; Uskokovic, M. R.; Snider, B. B. J. Am. Chem. Soc. 1981, 103, 1293.
4. Mikami, K.; Kawamoto, K.; Nakai, T. Tetrahedron Lett. 1985, 26, 5799
5. Mikami, K.; Kawamoto, K.; Nakai, T. Tetrahedron Lett. 1986, 27, 4899.
6. Castado, L; Granja, J. R.; Mourino, A. Tetrahedron Lett. 1985, 26, 4959.
7. Mikami, K.; Kawamoto, K.; Nakai, T. Chem. Lett. 1985, 115
8. Tanabe, M.; Hayashi, K. J. Am. Chem. Soc. 1980, 102, 862.
9. Koreeda, M.; Tanaka, Y.; Schwartz, A. J. Org. Chem. 1980, 45, 1172.
10. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1976, 98, 630
11. Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1978, 100, 3435
12. Takahashi, T.; Ootake, A.; Tsuji, J. Tetrahedron Lett. 1984, 25, 1921
13. Takahashi, T.; Ootake, A.; Tsuji, J.; Tachibana, K. Tetrahedron 1985, 41, 5747
14. Temple, J. S.; Schwartz, J. J. Am. Chem. Soc. 1980, 102, 7381.
15. Riediker, M.; Schwartz, J. Tetrahedron Lett. 1981, 22, 4655
16. Marino, J. P.; Abe, H. J. Am. Chem. Soc. 1981, 103, 2907
17. Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404
18. Wicha, J.; Bal, K. J. Chem. Soc., Perkin Trans. 1 1978, 1282.
19. Midland, M. M.; Kwon, Y. C. J. Am. Chem. Soc. 1983, 105, 3725
20. Midland, M. M.; Kwon, Y. C. Tetrahedron Lett. 1985, 26, 5017.
21. Binderup, L.; Latini, S.; Binderup, E.; Brettino, C.; Calverley, M.; Hansen, K. Biochem. Pharmacol. 1991, 42, 1569
22. Tsuji, J.; Yamakawa, T. Tetrahedron Lett. 1976, 613
23. Tsuji, J.; Shimizu, I.; Minami, I. Chem. Lett. 1984, 1017
24. Tsuji, J.; Shimizu, I.; Minami, I. Synthesis 1986, 623.
25. Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji, J. J. Org. Chem. 1992, 57, 1326
26. Moiseenkov, A. M.; Ceskis, B. A.; Semenovskii, A. V.; Bogoslovskii, N. A.; Litvinova, G. E.; Samokhvalov, G. I.; Segal, A. G.; Torgov, I. V. Bio org. Khim. 1983, 9, 118
27. Moiseenkov, A. M.; Ceskis, B. A.; Semenovskii, A. V.; Bogoslovskii, N. A.; Litvinova, G. E.; Samokhvalov, G. I.; Segal, A. G.; Torgov, I. V. Chem. Abstr. 1983, 98, 198577h
28. Narwid, T. A.; Cooney, K. E.; Uskokovic, M. R. Helv. Chim. Acta 1974, 57, 771.
29. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley Interscience; New York, 1988; p 77