Alcohol inversion of 17β-steroids

Inversion of 17β-steroids has been accomplished using a modified Mitsunobu protocol in which 4-nitrobenzoic acid is employed as the acidic component. Excellent yields of inverted product were obtained for a number of representative steroid families including estrogens, equilenins, and androgens. App...

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Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 6; no. 1; pp. 1 - 2
Main Authors Dodge, Jeffrey A., Lugar, Charles W.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 09.01.1996
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Summary:Inversion of 17β-steroids has been accomplished using a modified Mitsunobu protocol in which 4-nitrobenzoic acid is employed as the acidic component. Excellent yields of inverted product were obtained for a number of representative steroid families including estrogens, equilenins, and androgens. Application of this methodology to the synthesis of 17α-dihydroequilenin is described. Inversion of 17β-steroids has been examined using a modified Mitsunobu protocol in which 4-nitrobenzoic acid is employed as the acidic component. Excellent yields of inverted product were obtained for a number of representative steroid families including estrogens, equilenins, and androgens.
ISSN:0960-894X
1464-3405
DOI:10.1016/0960-894X(95)00559-C