Trofimov Reaction with Oximes Derived from Ketosteroids: Steroid-Pyrrole Structures |
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| Authors: | Zaitsev A. B. Vasil'tsov A. M. Shmidt E. Yu. Mikhaleva A. I. Afonin A. V. Il'icheva L. N. |
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| Affiliation: | (1) Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia |
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| Abstract: | Steroidal ketone oximes, namely pregnenolone oxime,  5-cholesten-3-one oxime, and progesterone dioxime react with acetylene in superbasic systems (Trofimov reaction) to afford steroid-pyrrole assemblies. The process is accompanied by prototropic migration of double bonds in the steroid fragment and vinylation of hydroxy groups in sterols with acetylene. The O-vinyl group can readily be removed by methanolysis. |
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