A Facile Synthesis of Both Enantiomers of 6-Acetoxy-5-hexadecanolide, a Major Component of Mosquito Oviposition Attractant Pheromones

被引：18

作者：

Singh, Surendra ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, Ctr Synth & Chem Biol, Sch Chem & Chem Biol, Dublin 4, Ireland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 12期

关键词：

Pheromones; Lactones; Natural products; Total synthesis; ASYMMETRIC ALDOL REACTIONS; CULEX-PIPENS-FATIGANS; STEREOSELECTIVE-SYNTHESIS; ENANTIOSPECIFIC SYNTHESIS; ERYTHRO-6-ACETOXY-5-HEXADECANOLIDE; (-)-(5R; 6S)-6-ACETOXY-5-HEXADECANOLIDE; 6S)-6-ACETOXYHEXADECANOLIDE; (5R; STEREOISOMERS; CATALYST;

D O I：

10.1002/ejoc.200801134

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of (-)-(5R,6S)-erythro-6-acetoxy-5-hexadecanolide, the major component of a mosquito oviposition attractant pheromone, and its enantiomer are reported. The synthesis was completed over seven steps in 28% overall yield by using Sharpless asymmetric epoxidation and ZrCl4-catalyzed cyclic acetal formation as the key steps. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：1896 / 1901

页数：6

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