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A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth

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Abstract

An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth has been achieved. Based on the asymmetric methylation of chiral (S)-4-benzyloxazolidin-2-one, the carbon chain of the target molecule was assembled through a C1+C10+C4+C3 procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid and then, with the induction of Evan’s template, a chiral methyl group was introduced to the position of the carboxylic group in 97% de. After reduction and a couple of chemical operations, the designed key intermediate A1 was obtained. The synthesis of another moiety was started from decane-1,10-diol which was selectively protected and oxidized. The long carbon chain was installed according to a Wittig protocol. After deprotection, oxidization, and methylenation, the target molecule was synthesized in 7 linear steps with an overall yield of 30.3%.

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ACKNOWLEDGMENTS

The authors thank Liang Zhu Huang for the hydrogenation steps, technician Hong Li Zhang for the NMR analysis, and Yao-Xiang Duan for HRMS detection.

Funding

This research was funded by an NSFC grant number [31301712, 31760639]. Partial financial support from the Jiangxi technological normal university is greatly appreciated. Zhen-Ting Du thanks Opening Funds of Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, and the Chinese Academy of Sciences for partial financial support.

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Authors and Affiliations

  1. Xinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin, Tarim University, 843300, Alar, China

    Liang Wei, Guo-Guo He & Hongjin Bai

  2. College of Chemistry and Pharmacy, Northwest A&F University, 712100, Yangling, China

    Lu Liu, Meng Tang, Tao Zhang & Zhen-Ting Du

  3. Key Laboratory of Functional Small Organic Molecules, Ministry of Education, 330027, Nanchang, Jiangxi Province, China

    Zhen-Ting Du

  4. Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, 712100, Yangling, China

    Zhen-Ting Du

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  1. Liang Wei
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  2. Guo-Guo He
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  3. Lu Liu
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  4. Meng Tang
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  5. Tao Zhang
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Correspondence to Hongjin Bai or Zhen-Ting Du.

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Wei, L., He, GG., Liu, L. et al. A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth. Russ J Org Chem 56, 1089–1095 (2020). https://doi.org/10.1134/S1070428020060196

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