Abstract
Steroidal ketone oximes, namely pregnenolone oxime, Δ5-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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Zaitsev, A.B., Vasil'tsov, A.M., Shmidt, E.Y. et al. Trofimov Reaction with Oximes Derived from Ketosteroids: Steroid-Pyrrole Structures. Russian Journal of Organic Chemistry 39, 1406–1411 (2003). https://doi.org/10.1023/B:RUJO.0000010554.30452.01
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DOI: https://doi.org/10.1023/B:RUJO.0000010554.30452.01