Defensive mechanisms of arthropods .144. Absolute configuration of insect-produced epilachnene

被引：19

作者：

Farmer, JJ

Attygalle, AB

Smedley, SR

Eisner, T

Meinwald, J

机构：

[1] CORNELL UNIV,DEPT CHEM,BAKER LAB,ITHACA,NY 14853

[2] CORNELL UNIV,NEUROBIOL & BEHAV SECT,ITHACA,NY 14853

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 16期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)00490-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Samples of (R) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en-14-olide] were synthesized from (R) and(S)-norvaline. The diastereomeric alpha-methoxy-alpha-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) alpha-methoxy-alpha-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene. (C) 1997 Elsevier Science Ltd.

引用

页码：2787 / 2790

页数：4

共 12 条

[1] AZAMACROLIDES - A FAMILY OF ALKALOIDS FROM THE PUPAL DEFENSIVE SECRETION OF A LADYBIRD BEETLE (EPILACHNA-VARIVESTIS) [J].