Trofimov Reaction with Oximes Derived from Ketosteroids: Steroid-Pyrrole Structures

Autor:	L. N. Il'icheva, Alexey B. Zaitsev, A. I. Mikhaleva, Andrei V. Afonin, A. M. Vasil'tsov, E. Yu. Shmidt
Rok vydání:	2003
Předmět:	chemistry.chemical_classification Ketone Double bond Chemistry medicine.medical_treatment Organic Chemistry Oxime Medicinal chemistry Steroid chemistry.chemical_compound Acetylene medicine Pregnenolone Pyrrole medicine.drug
Zdroj:	Russian Journal of Organic Chemistry. 39:1406-1411
ISSN:	1070-4280
DOI:	10.1023/b:rujo.0000010554.30452.01
Popis:	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.
Databáze:	OpenAIRE
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