Asymmetric synthesis of polyacetate derived building blocks with α-oxyanion functionality.: Lewis acid catalyzed opening of 2,9-dioxabicyclo[3.3.1]nonan-3-ones

被引：28

作者：

Dunkel, R ^{[1
]}

Hoffmann, HMR ^{[1
]}

机构：

[1] Leibniz Univ Hannover, Dept Organ Chem, D-30167 Hannover, Germany

来源：

TETRAHEDRON | 1999年 / 55卷 / 28期

关键词：

D O I：

10.1016/S0040-4020(99)00460-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

All four stereoisomeric cyclic 3,5,7-trihydroxyheptanoic acid equivalents of the polyacetate aldol type (Scheme 1) are obtainable from 8-oxabicyclo[3.2.1]octd-en-3-one which functions as a meso-configurated 4-way optical switch. Lewis acid assisted nucleophilic ring opening of anomeric [3.3.1] oxabicyclic lactones is a key step. The utility of the methodology is exemplified by a 6 step synthesis of the C17-C23 fragment of spongistatin (altohyrtin) and C-glycoside analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8385 / 8396

页数：12

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