Inhibitors of Steroid Biosynthesis: Preparation of 5,10-Secoestr-4-ynes

Douglas F. Covey, Vinod D. Parikh

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

This paper describes two novel syntheses of 5,10-secoestr-4-yne-3,10,17-trione, a compound which has been shown previously to be a powerful irreversible inhibitor of both bacterial and mammalian Δ5-3-keto steroid isomerases. One synthetic route makes available 3β-hydroxy-4-acetylenic 5,10-seco steroids and the other provides 3α-hydroxy-4-acetylenic 5,10-seco steroids. Stereospecific routes to these epimeric α,β-acetylenic alcohols were developed because of their potential utility as mechanism-based inhibitors of the corresponding 3α- and 3β-hydroxy steroid dehydrogenases.

Original languageEnglish
Pages (from-to)5315-5318
Number of pages4
JournalJournal of Organic Chemistry
Volume47
Issue number27
DOIs
StatePublished - Jan 1 1982

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