SYNTHESIS AND ENANTIOMERIC PURITY DETERMINATION OF THE OPTICALLY-ACTIVE EPOXIDE DISPARLURE, SEX-PHEROMONE OF THE GYPSY-MOTH

被引：42

作者：

PIRKLE, WH

RINALDI, PL

机构：

[1] The Roger Adams Laboratory, School of Chemical Sciences, University of Illinois, Urbana

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 07期

关键词：

D O I：

10.1021/jo01321a001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure (+)-cis-7(R), 8(S)-epoxy-2-methyloctadecane (disparlure, la), the sex pheromone of Porthetria dispar (L.), has been synthesized in 12% yield by a five-step sequence of reactions. By the same technique, (−)-trans-1 has been prepared in similar yield, [α]24D-23.6°. The sequence can be used to prepare cis- and/ or trans-1 in racemic or enantiomerically pure form. 13C NMR of the immediate precursor to 1, in the presence of chiral lanthanide shift reagent, allows the determination of its enantiomeric purity. © 1979, American Chemical Society. All rights reserved.

引用

页码：1025 / 1028

页数：4

共 13 条

[1]

BESTMANN HJ, 1974, TETRAHEDRON LETT, P207

[2] POTENT SEX ATTRACTANT OF GYPSY MOTH - ITS ISOLATION, IDENTIFICATION, AND SYNTHESIS [J].