Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols

Malcolm M Campbell, Raymond C Craig, Andrew C. Boyd, Iain M. Gilbert, Robert T. Logan, James Redpath, Robert G. Roy, David S. Savage, Thomas Sleigh

Research output: Contribution to journalArticle

Abstract

The seven possible 3-amino-2-hydroxy and 2-amino-3-hydroxy isomers of the anti-arrhythmic steroid, 3a-amino-2ß-hydroxy-5a-androstan-17- one, were prepared from 5a-androst-2-en-17-one. The intermediate 2a,3a- and 2ß,3ß-epoxides and aziridines were cleaved to vicinal trans-diaxial amino- and azido-alcohols, which in turn yielded the isomers by a series of functional group inversions and transformations.

Original languageEnglish
Pages (from-to)2235-2247
Number of pages13
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1979

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    Campbell, M. M., Craig, R. C., Boyd, A. C., Gilbert, I. M., Logan, R. T., Redpath, J., Roy, R. G., Savage, D. S., & Sleigh, T. (1979). Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols. Journal of the Chemical Society, Perkin Transactions 1, 2235-2247.