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Citation: WU Ming-Hu, LI Yan, CHEN Zu-Xing, YANG Gui-Chun, SHI Cong-Yun. A Novel Method for Synthesis of Insect Sex Pheromone S-(+)-Sulcatol[J]. Chinese Journal of Applied Chemistry, ;2000, 17(2): 224-226. shu

A Novel Method for Synthesis of Insect Sex Pheromone S-(+)-Sulcatol

1.
a Department of Chemistry, Xianning Normal College, Xianning 437005;
2.
b Faculty of Chemistry and Material Science, Hubei University, Wuhan

Received Date: 3 September 1999
Available Online: 23 November 1999
Fund Project: 湖北省教委重点资助课题(96A077) (96A077)

The S-(+)-sulcatol(1) was prepared in 4 steps. Sodium phenyl sulfinate was reacted with bromoacetone in ethanol to give 1-phenylsulfonyl-2-propanone(2). Alkylation of (2) by 1-chloro-3-methyl-2-butene(3) in the presence of K₂CO₃ through solid-liquid PTC in DMF at 40~50℃ gave 3-phenylsulfonyl-6-methyl-5-heptene-2-one(4). The sulfone moiety of (4) was removed by Raney Ni reduction under mild conditions and the key intermediate prochiral 6-methyl-5-heptene-2-one(5) was obtained. Sulcatol(1) with optical purity of 94% e.e. was obtained by Baker's yeast mediated reduction of (5).
- ambrosia beetle,
- insect sex pheromone,
- asymmetric synthesis
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