STEREOCONTROLLED SYNTHESIS OF CYCLIC ETHERS BY INTRAMOLECULAR HETERO-MICHAEL ADDITION .4. ENANTIOMERIC SYNTHESIS OF SUBSTITUTED AND FUSED OXEPANES

被引：42

作者：

SOLER, MA ^{[1
]}

PALAZON, JM ^{[1
]}

MARTIN, VS ^{[1
]}

机构：

[1] UNIV LA LAGUNA,CTR PROD NAT ORGAN ANTONIO GONZALEZ,INST BIOORGAN,CARRETERA LA ESPERANZA 2,E-38206 LA LUGUNA,SPAIN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(00)73937-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of an intramolecular hetero-Michael addition of enantiomerically enriched 7-alkoxy4-benzoyloxy-2,3-unsaturated esters for the synthesis of endo-substituted oxepanes is described, The stereochemistry in the cyclization step is governed by the geometry of the double bond in the unsaturated ester and the presence of a Z-double bond in the linear chain is required in order to achieve good yields. The synthesis of the fused oxepane-tetrahydropyran nucleus of marine polyether toxins with absolute control of all the stereocentres is described.

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页码：5471 / 5474

页数：4

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