Enantioselective synthesis of ceralure B1, ethyl cis-5-iodo-trans-2-methylcyclohexane-1-carboxylate

被引：17

作者：

Raw, AS ^{[1
]}

Jang, EB

机构：

[1] USDA ARS, PSI, Insect Chem Ecol Lab, Beltsville, MD 20705 USA

[2] USDA ARS, Trop Fruit & Vegetable Res Lab, Hilo, HI 96720 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 21期

关键词：

insects; asymmetric synthesis; regiochemistry;

D O I：

10.1016/S0040-4020(00)00219-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl (1R, 2R, SR)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent attractant for the Mediterranean fruit fly. This compound was stereoselectively synthesized on a multigram scale in nine steps in 15% yield. Key steps of the synthesis involved an asymmetric Diels-Alder reaction, iodolactonization, stereoselective reduction of the carbonyl, and inversion of configuration with iodide. Published by Elsevier Science Ltd.

引用

页码：3285 / 3290

页数：6

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