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Issue 0, 1979
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Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols

Abstract

The seven possible 3-amino-2-hydroxy and 2-amino-3-hydroxy isomers of the anti-arrhythmic steroid, 3α-amino-2β-hydroxy-5α-androstan-17-one, were prepared from 5α-androst-2-en-17-one. The intermediate 2α, 3α- and 2β,3β-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.

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Article type: Paper
DOI: 10.1039/P19790002235
J. Chem. Soc., Perkin Trans. 1, 1979, 2235-2247

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

    M. M. Campbell, R. C. Craig, A. C. Boyd, I. M. Gilbert, R. T. Logan, J. Redpath, R. G. Roy, D. S. Savage and T. Sleigh, J. Chem. Soc., Perkin Trans. 1, 1979, 2235
    DOI: 10.1039/P19790002235

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