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Issue 0, 1971
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Applications of high-potential quinones. Part VII. The synthesis of steroidal phenanthrenes by double methyl migration

Abstract

Steroidal phenanthrenes are formed from 17 α-methyl-Δ9(11)-testosterones by the action of dichlorodicyanobenzoquinone and toluene-p-sulphonic acid in refluxing dioxan. Initial dehydration occurs without rearrangement to give δ16-derivatives, which undergo double methyl migration and oxidation to the phenanthrenes. Isolation of the Δ16-intermediates is ascribed to the presence of the Δ9(11)-bond, which eliminates the usual 11 β-H–13-Me diaxial interaction in ring C.

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Article type: Paper
DOI: 10.1039/J39710002566
Citation: J. Chem. Soc. C, 1971,0, 2566-2572
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    Applications of high-potential quinones. Part VII. The synthesis of steroidal phenanthrenes by double methyl migration

    W. Brown and A. B. Turner, J. Chem. Soc. C, 1971, 0, 2566
    DOI: 10.1039/J39710002566

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