An alternative enantioselective synthesis of (+)-tricyclodecadienone

被引：9

作者：

Knol, J ^{[1
]}

Feringa, BL ^{[1
]}

机构：

[1] UNIV GRONINGEN, GRONINGEN CTR CATALYSIS & SYNTH, DEPT ORGAN & MOL INORGAN CHEM, NL-9747 AG GRONINGEN, NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 14期

关键词：

GAMMA-ALKOXYBUTENOLIDES; ASYMMETRIC-SYNTHESIS; CLAVULONES; ROUTE;

D O I：

10.1016/S0040-4039(97)00392-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiomerically pure endo-cycloadduct (2) under bar obtained from the thermal Diels-Alder reaction of SR-(1-menthyloxy)-2(5H)-furanone with cyclopentadiene is converted into (+)-tricyclo[5.2.1.0(2,6)]decadi-4,8-en-3-one ((+)-(1) under bar) in a one-pot procedure via ring-opening with lithium methyl dimethylphosphonate followed by an intramolecular Wittig-Horner-Emmons reaction in THF. The use of LiBr as additive in this step is highly beneficial to the formation of (1) under bar. (C) 1997 Published by Elsevier Science Ltd.

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页码：2527 / 2530

页数：4

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