STEREOSELECTIVE INTRAMOLECULAR CYCLOPROPANATIONS - ENANTIOSELECTIVE SYNTHESES OF 1-ALPHA,25-DIHYDROXYVITAMIN D-3 A-RING PRECURSORS

被引：16

作者：

DAUBEN, WG

HENDRICKS, RT

PANDY, B

WU, SC

ZHANG, XM

LUZZIO, MJ

机构：

[1] Department of Chemistry, University of California, Berkeley

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 14期

关键词：

D O I：

10.1016/0040-4039(95)00284-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two efficient enantioselective syntheses of an A-ring precursor to 1 alpha,25-dihydroxyvitamin D-3 have been developed. The key step in these sequences involves the stereoselective cyclopropanation of a chiral gamma-alkoxy-alpha-diazo-beta-keto ester. In one sequence, the 1 alpha-hydroxy group was introduced in the first step by a diastereoselective ene reaction and in the other sequence by use of (S)-malic acid as starting material. Both routes eliminate the need for a SeO2 oxidation.

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页码：2385 / 2388

页数：4

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