Alcohol inversion of 17β-steroids

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 1, 1996, Pages 1-2

  Dodge, Jeffrey A ^a   Lugar III, Charles W ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

17ALPHA DIHYDROEQUILENIN; ANDROGEN; EQUILENIN; ESTROGEN; STEROID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030052169     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(95)00559-C     Document Type: Article

References (20)

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2. Clark, J. H.; Markaverich, B. M. Pharmacol. Ther. 1982, 21, 429.
3. Reduction of 17-ketones occur exclusively from the α-face to provide the corresponding 17β-alcohol. See Feiser, L. F.; Fieser, M., Ed., Steroid, Reinhold Publishing Corporation, New York, 1959, p 444.
4. Bose, A. K.; Lal. B.; Hoffman, W. A.; Manhas, M. S. Tetrahedron Lett. 1973, 18, 1619.
5. (a) Mitsunobu, O Synthesis 1961, 1.
6. (b) Hughes, D. L. Org. React. 1992, 42, 335.
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8. For reasons that are not entirely clear, increases in yields under Mitsunobu conditions have been reported in the steroid nucleus when benzene is used as die solvent See Loibner, H.; Zbiral, E. Helv. Chim. Acta 1977, 60, 417.
9. (a) Gabbard, R. B.; Segaloff, A. Steroids 1963, 42, 3195.
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13. (b) Tsunoda, T.; Nagaku, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H., Ito, S. Tetrahedron Lett. 1995, 36, 2531.
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17. For other variations see (a) Tsunoda, T.; Ozaki, F.; Ito, S. Tetrahedron Lett. 1994, 35, 5081.
18. (b) Castro, J. L.; Matassa, V. G. J. Org. Chem. 1994, 59, 2289.
19. Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem. 1994, 59, 234.
20. All new compounds exhibited appropriate 1H-NMR, IR, MS and/or elemental analysis.