CONVENIENT SYNTHESIS OF MOSQUITO OVIPOSITION PHEROMONE AND A HIGHLY FLUORINATED ANALOG RETAINING BIOLOGICAL-ACTIVITY

被引：32

作者：

DAWSON, GW ^{[1
]}

MUDD, A ^{[1
]}

PICKETT, JA ^{[1
]}

PILE, MM ^{[1
]}

WADHAMS, LJ ^{[1
]}

机构：

[1] UNIV LONDON LONDON SCH HYG & TROP MED,LONDON WC1E 7HT,ENGLAND

来源：

JOURNAL OF CHEMICAL ECOLOGY | 1990年 / 16卷 / 06期

关键词：

acetoxyhexadecanolide; attractant; Culex quinquefasciatus; Culicidae; Diptera; Mosquito; oviposition; perfluoroalkyl; pheromone; pheromone analog; synthesis;

D O I：

10.1007/BF01020494

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A simple three-step synthesis is described for 6-acetoxy-5-hexadecanolide, the oviposition pheromone of the mosquito Culex quinquefasciatus Say and others in that genus. An aldol condensation between 1-trimethylsilyloxycyclopent-1-ene and undecanal, followed by Baeyer-Villiger ring expansion and acetylation, gave the required compound as a 1:1 mixture of diastereoisomers in high overall yield (>80%). This synthetic approach is readily adapted for synthesis of analogs. The heptadecafluoro compound, in which the n-octyl group is replaced by perfluorooctyl, retained high biological activity. © 1990 Plenum Publishing Corporation.

引用

页码：1779 / 1789

页数：11

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