Selective ring-opening carbonylation of epoxy-steroids

Ring-opening alkoxycarbonylation of epoxy-steroids has been carried out with a Co 2(CO) 8/3-hydroxypyridine catalytic system. High chemo- and regioselectivities were obtained under the reaction conditions applied. Structural analysis of the products proved their high stereochemical purity in each ca...

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Veröffentlicht in:	Steroids 2004-04, Vol.69 (4), p.271-277
Hauptverfasser:	Balázs, Attila, Benedek, Csilla, Szalontai, Gábor, Tőrös, Szilárd
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkoxycarbonylation Asymmetric ring-opening Biological and medical sciences Catalysis Chromatography, Gas Chromatography, Thin Layer Cobalt Epoxy Compounds - chemistry Epoxy-steroid Fundamental and applied biological sciences. Psychology Furans - chemistry Homogeneous catalysis Magnetic Resonance Spectroscopy Molecular Structure Solutions Stereoisomerism Steroids - chemistry Structure-Activity Relationship Substrate Specificity Vertebrates: endocrinology
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Beschreibung
Zusammenfassung:	Ring-opening alkoxycarbonylation of epoxy-steroids has been carried out with a Co 2(CO) 8/3-hydroxypyridine catalytic system. High chemo- and regioselectivities were obtained under the reaction conditions applied. Structural analysis of the products proved their high stereochemical purity in each case, accompanied by inversion of the original configuration. No carbonylation took place for sterically hindered steranic epoxides.
ISSN:	0039-128X 1878-5867
DOI:	10.1016/j.steroids.2004.02.003