CARBOHYDRATES TO CARBOCYCLES - A SYNTHESIS OF (-)-ALPHA-PIPITZOL

被引：41

作者：

PAK, H ^{[1
]}

CANALDA, II ^{[1
]}

FRASERREID, B ^{[1
]}

机构：

[1] DUKE UNIV,PAUL M GROSS CHEM LAB,DEPT CHEM,DURHAM,NC 27706

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 10期

关键词：

D O I：

10.1021/jo00297a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 2-deoxy-3-keto sugar derived from methyl a-D-mannopyranoside has been processed to give a multibranched-chain sugar which undergoes serial radical cyclization, affording a pyranosidodiquinane as the key intermediate. The diquinane moiety represents the BC ring system of pipitzol, the A ring being obtained from the pyranosido moiety. A late intermediate is identified by comparison with the racemic modification prepared by Funk and Bolton, and, following their procedure, (-)-α-pipitzol was obtained spectroscopically identical with the racemic modification but with [a]D = -141°. © 1990, American Chemical Society. All rights reserved.

引用

页码：3009 / 3011

页数：3

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