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First Example of Construction of a Pyrrole Ring Bonded to a Steroid System by the Trofimov Reaction
Authors:A. M. Vasil'tsov  E. Yu. Shmidt  A. I. Mikhaleva  A. V. Afonin  A. B. Zaitsev
Affiliation:(1) Irkutstk A. E. Favorsky Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033
Abstract:The oxime of Delta5-pregnen-3beta-ol-20-one reacts with acetylene in the KOH-DMSO system to form a mixture of products containing 3beta-vinyloxy-17beta-(1-vinyl-2-pyrrolyl)-Delta5-androstene as the major product (63% yield) and also the O-vinyloxime of 3beta-vinyloxy-Delta5-pregnen-20-one (10%), 3beta-vinyloxy-17agr- and 3beta-vinyloxy-17beta-Delta5-pregnen-20-one (25%, 1:4 ratio).
Keywords:acetylene  pregnenolone oxime  pyrroles  steroids
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