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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 11: 4437 - 4443

DOI: https://doi.org/10.6023/cjoc202107005

ARTICLES

Asymmetric Synthesis of (3Z,6Z,9S,10R)-9,10-Epoxy-3,6-heneicosadiene, Sex Pheromone Component of Hyphantria cunea

  • Gucheng Yuan ,
  • Jiawei Liu ,
  • Shihang Yu ,
  • Chaonan Yuan ,
  • Qinghua Bian ,
  • Min Wang ,
  • Jiangchun Zhong
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  • College of Science, China Agricultural University, Beijing 100193
† These authors contributed equally to this work.
* Corresponding author. E-mail:

Received date: 2021-07-02

  Revised date: 2021-07-17

  Online published: 2021-08-10

Supported by

National Key Research and Development Program of China(2017YFD0201404)

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Abstract

Hyphantria cunea is an important worldwide pest due to its destructiveness to the crops and trees. The main active component of its sex pheromone is (3Z,6Z,9S,10R)-9,10-epoxy-3,6-henicosadiene. A new synthesis of the sex pheromone from 1-bromoundecane was developed. The procedure includes 11 steps, and the overall yield is 14%. Furthermore, nucleophilic substitution of alkyl halide, partial hydrogenation with nickel boride, Sharpless asymmetric epoxidation, ring opening with HClO4, and alkylative epoxide rearrangement (invovling the ring opening of terminal epoxide and the ring-closure with K2CO3) are crucial steps.

Key words： Hyphantria cunea; synthesis of pheromone; Sharpless asymmetric epoxidation; alkylative epoxide rearrangement

Cite this article

Gucheng Yuan , Jiawei Liu , Shihang Yu , Chaonan Yuan , Qinghua Bian , Min Wang , Jiangchun Zhong . Asymmetric Synthesis of (3Z,6Z,9S,10R)-9,10-Epoxy-3,6-heneicosadiene, Sex Pheromone Component of Hyphantria cunea[J]. Chinese Journal of Organic Chemistry, 2021 , 41(11) : 4437 -4443 . DOI: 10.6023/cjoc202107005

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