Abnormal Beckmann fragmentation/ring closing metathesis route for preparation of 18-nor-Delta-androgens and their 18-nor-13,17-epoxide derivatives期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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Abnormal Beckmann fragmentation/ring closing metathesis route for preparation of 18-nor-Delta-androgens and their 18-nor-13,17-epoxide derivatives

Authors:	Wang Cunde Rath Nigam P Covey Douglas F

Institution:	^a Department of Molecular Biology and Pharmacology, Washington University School of Medicine, 660 South Euclid Avenue, St. Louis, MO 63110, USA ^b Department of Chemistry and Biochemistry, University of Missouri St. Louis, 8001 Natural Bridge Road, St. Louis, MO 63121, USA

Abstract:	The synthesis of 18-nor-Δ¹³⁽¹⁷⁾-androgens and the structurally related 13,17-epoxides is described. The synthetic route involves the cleavage of 17-ketosteroids by an abnormal Beckmann rearrangement, modification of the D-ring cleavage product to obtain an intermediate tricyclic diene and ring closing metathesis of the diene to the 18-nor-Δ¹³⁽¹⁷⁾-androgen. (3α,5α)-18-Norandrost-13(17)-en-3-ol and the derivative 13α,17α- and 13β,17β-epoxides were prepared by this route.

Keywords:	Olefin metathesis 18-Nor-Δ¹³⁽¹⁷⁾-steroids 18-Nor-13 17-epoxysteroids Abnormal Beckmann rearrangement Neurosteroids
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