A NEW AND EFFICIENT ASYMMETRIC-SYNTHESIS OF AN A-RING PRECURSOR TO PHYSIOLOGICALLY ACTIVE 1-ALPHA-HYDROXYVITAMIN D3 STEROIDS

被引：36

作者：

POSNER, GH

CARRY, JC

ANJEH, TEN

FRENCH, AN

机构：

[1] Department of Chemistry, Johns Hopkins University, Baltimore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 26期

关键词：

D O I：

10.1021/jo00052a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereocontrolled and mild Diels-Alder cycloaddition involving stereochemically matched pyrone (S)-lactate 4 and Lewis acid (-)-Pr(hfc)3 produced bicyclic lactone endo-5 via a double stereodifferentiation process. Bicyclic lactone 5 was then transformed smoothly and in high yield into phosphine oxide (-)-1, an important A-ring precursor to various physiologically active 1alpha-hydroxyvitamin D3 steroids.

引用

页码：7012 / 7014

页数：3

共 36 条

[11] ACYCLIC STEREOSELECTION .12. DOUBLE STEREODIFFERENTIATION WITH MUTUAL KINETIC RESOLUTION - A SUPERIOR CLASS OF REAGENTS FOR CONTROL OF CRAMS RULE STEREOSELECTION IN SYNTHESIS OF ERYTHRO-ALPHA-ALKYL-BETA-HYDROXY CARBOXYLIC-ACIDS FROM CHIRAL ALDEHYDES [J].