Amino-steroids. Part 7. The synthesis of 3α-amino-2β-hydroxy- and 2β-amino-3α-hydroxy-androst-5-en-17-one

Malcolm M Campbell, Raymond C Craig, James Redpath, David S. Savage, Thomas Sleigh

Research output: Contribution to journalArticle

Abstract

Stereospecific transformations of 5a6ß-dichloroandrost-2-en-17- one into 3a-amino-2ß-hydroxyandrost-5-en-17-one and 2ß-amino-3a-hydroxyandrost-5-en-17-one have been achieved via the ?5-2ß,3ß- and 2a,3a-epoxides. Direct treatment of the 5a,6ß-dichloro-2ß,3ß-epoxide with sodium azide gave 3a,6a-bisazido-2ß-hydroxyandrost-4-en-17-one, while the 5a,6ß-dichloro-2a,3a-epoxide gave 2ß,6a-bisazido-3a-hydroxyandrost-4-en-17-one.

Original languageEnglish
Pages (from-to)3042-3047
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1979

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