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Issue 1, 1978
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Unsaturated steroids. Part 9. Synthesis of some aromatic ring c steroids

Richard Edmunds,  John M. Midgley,  Linda G. Tagg,  Brian J. Wilkins  and  W. Basil Whalley 

Abstract

7α,11α,22α,23α-Tetrabromo-5α-ergost-8-en-3β-yl acetate (1) has been aromatised to 22α,23α-dibromo-12-methyl-18-nor-5α-ergosta-8,11,13-trien-3β-yl acetate (2) in solution by using an acidic catalyst. Stepwise removal of the side-chain from 12-methyl-18-nor-5α-ergosta-8,11,13,22-tetraen-3β-yl acetate (5) afforded successively the C-22 aldehyde (6), the C-20 ketone (8), and 3β-hydroxy-12-methyl-18-nor-5α-androsta-8,11,13-trien-17-one (18). Associated derivatives are described; certain reaction mechanisms have been clarified.

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Article type: Paper
DOI: 10.1039/P19780000076
Citation: J. Chem. Soc., Perkin Trans. 1, 1978,0, 76-80
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    Unsaturated steroids. Part 9. Synthesis of some aromatic ring c steroids

    R. Edmunds, J. M. Midgley, L. G. Tagg, B. J. Wilkins and W. B. Whalley, J. Chem. Soc., Perkin Trans. 1, 1978, 0, 76
    DOI: 10.1039/P19780000076

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