Tetrahedron: Asymmetry

Asymmetric total synthesis of all four isomers of 6-acetoxy-5-hexadecanolide: the major component of mosquito oviposition attractant pheromones

HB Dong, MY Yang, XT Zhang, MA Wang

文献索引：Dong, Hong-Bo; Yang, Ming-Yan; Zhang, Xiao-Teng; Wang, Ming-An Tetrahedron Asymmetry, 2014 , vol. 25, # 8 p. 610 - 616

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被引用次数: 3

摘要

Abstract An asymmetric total synthesis of (5S, 6R)-(+)-erythro-6-acetoxy-5-hexadecanolide 1a has been accomplished from readily available hex-5-yn-1-ol via Shi's asymmetric epoxidation as the key step, in eight steps with an overall yield of 33.5%. In addition, the stereoselective synthesis of all four isomers of 6-acetoxy-5-hexadecanolide 1a–1d were obtained via Sharpless asymmetric dihydroxylation and Mitsunobu reaction as the key ...