STEREOSELECTIVE SYNTHESIS OF SYN-1,3-DIOL ACETONIDES BY REDUCTIVE DECYANATION OF CYANOHYDRINS

被引：58

作者：

RYCHNOVSKY, SD

ZELLER, S

SKALITZKY, DJ

GRIESGRABER, G

机构：

[1] Department of Chemistry, University of Minnesota, Minneapolis

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 21期

关键词：

D O I：

10.1021/jo00308a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: syn- l,3-Diol acetonides are produced with >99:1 selectivity by reductive decyanation of the corresponding cyanohydrin acetonides. Cyanohydrin acetonides (4,6-dialkyl-4-cyano-2,2-dimethyl-l,3-dioxanes) are available from 3-hydroxy aldehydes by cyanohydrin formation and alkylation, or directly from 0-hydroxy ketones. The former method is particularly well suited to the convergent synthesis of alternating (1,3,5,) polyol chains which are found in the polyene macrolide antibiotics1. © 1990, American Chemical Society. All rights reserved.

引用

页码：5550 / 5551

页数：2

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