A new strategy for the preparation of 11-oxygenated steroids synthesis of (±)-adrenosterone

被引：29

作者：

Grieco, PA ^{[1
]}

May, SA ^{[1
]}

Kaufman, MD ^{[1
]}

机构：

[1] Montana State Univ, Dept Biochem & Chem, Bozeman, MT 59717 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 39期

关键词：

D O I：

10.1016/S0040-4039(98)01526-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate 1,4-addition of 1-[(tert-butyldimethylsilyl)oxy]-2methyl-1,3-cyclohexadiene (5) to 2-methylcyclopentenone in highly polar media and subsequent alkylation of the resultant silyl enol ether (4) with phenylthiodienyl carbonate 10 in 5.0 M LiClO4. Et2O provides substrate 2. Exposure of 2 to TMSOTf/ TMSOCH2CH2OTMS affords tetracyclic bis-ketal 3, which is converted into (+/-)-adrenosterone (1) in four steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7047 / 7050

页数：4

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