Tetrahedron

Synthesis, crystal and molecular structure, and hyperconjugation of the isomeric 17, 20-epoxy-17-picolyl derivatives of 5-androstene and 5α-androstane

D Miljković, K Gas̆i, M Kindjer, S Stanković, G Argay

Index: Miljkovic, Dusan; Gasi, Katarina; Kindjer, Marija; Stankovic, Slobodanka; Argay, Gyula Tetrahedron, 1987 , vol. 43, # 3 p. 631 - 641

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Citation Number: 7

Abstract

Three pairs of isomeric 17, 20-epoxy-17-picolyl-derivatives of 5-androstene and 5α- androstane (3–8) have been prepared by an oxidation of 3β-acetoxy-17-picolinylidene- androst-5-ene (2) and 3β-acetoxy-17-picolinylidene-5α-androstane (2) with in situ prepared Cr (VI) oxide-pyridine-complex in methylene chloride at room temperature. X-Ray structural analysis of the suitably crystalline epoxides 5 and 6 revealed the structure of 5 being 17α, ...