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The Formation of Five-and Six-membered Rings by the Acyloin Condensation. VI. Cyclization of the Cholesterol a Ring via a 2, 3-Secodiester

JC Sheehan, WF Erman

文献索引:Sheehan et al. Journal of the American Chemical Society, 1957 , vol. 79, p. 147,148

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被引用次数: 20

摘要

Cyclization of 2, 3-secocholestane-2, 3-dioic acid dimethyl ester (I) by an acyloin condensation in homogeneous medium afforded a mixture, from which an acyloin assigned the structure 3@-hgdroxycholestane-2-one (11) was isolated in 82% yield. Minor products of the reaction were an isomeric 2-hydroxycholestane-3-one, cholestane-2a, 3@-diol, and 2, 3- secocholestanr-2, 3-dioic acid. Reduction of the acetate derivative of I1 with sodium ...