Synthesis of (R)-and (S)-enantiomers of the sex  pheromone of caddisfly (hesperophylax occidentalis)

Abstract

(R)-and (S)-6-methyl-3-nonanones, the sex pheromone produced by female caddisfly (Hesperophylax Occidentalis) were synthesized from R-camphor derivative-bornane-10,2-sultam via asymmetric Michael addition reaction of N-(E-2-enoyl) bornane-10,2-sultam with an alkyl magnesium reagent, reductive cleavage with LiAlH4, iodination of 3- methyl-1-hexanol and reaction of dialkyl cadmium with propionyl chloride. The enantiomeric excess of the total synthesis was over 96% ee.

Key words: CAMPHOR, SEX PHEROMONE, MICHAEL ADDITION REACTION

CLC Number:

O629

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Li Yan;Huang Jinxia;Ma Xingquan;Zhou Zhongqiang. Synthesis of (R)-and (S)-enantiomers of the sex pheromone of caddisfly (hesperophylax occidentalis)[J]. Chin. J. Org. Chem., 2001, 21(6): 463-466.

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(R)-和(S)-石蚕蛾属于信息素的合成

Synthesis of (R)-and (S)-enantiomers of the sex pheromone of caddisfly (hesperophylax occidentalis)

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