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This is an early access version, the complete PDF, HTML, and XML versions will be available soon.
Article

Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, Lyclene dharma dharma, and Their Enantiomers

by
Yun Zhou
1,
Jianan Wang
2,
Yueru Zhang
1,
Xiaochen Fu
1,
Hongqing Xie
1,
Jinlong Han
1,
Jianhua Zhang
1,
Jiangchun Zhong
2 and
Chenggang Shan
1,*
1
Institute of Industrial Crops, Shandong Academy of Agricultural Sciences, Jinan 250100, China
2
Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(12), 2918; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29122918
Submission received: 20 May 2024 / Revised: 14 June 2024 / Accepted: 18 June 2024 / Published: 19 June 2024
(This article belongs to the Special Issue Synthesis of Bioactive Compounds: Volume II)
Review Reports Versions Notes

Abstract

The Lichen moth, Lyclene dharma dharma (Arctiidae, Lithosiinae), plays a significant role in forest ecosystem dynamics. A concise and novel method to synthesize the active sex pheromone components, (S)-14-methyloctadecan-2-one ((S)-1), (S)-6-methyloctadecan-2-one ((S)-2), and their enantiomers has been developed. Key steps in the synthesis include the use of Evans’ chiral auxiliaries, Grignard cross-coupling reactions, hydroboration–oxidation, and Wacker oxidation. The synthesized sex pheromone components hold potential value for studies on communication mechanisms, species identification, and ecological management.
Keywords: sex pheromone; Lyclene dharma dharma; Evans’ chiral auxiliary; enantioselective synthesis sex pheromone; Lyclene dharma dharma; Evans’ chiral auxiliary; enantioselective synthesis

Share and Cite

MDPI and ACS Style

Zhou, Y.; Wang, J.; Zhang, Y.; Fu, X.; Xie, H.; Han, J.; Zhang, J.; Zhong, J.; Shan, C. Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, Lyclene dharma dharma, and Their Enantiomers. Molecules 2024, 29, 2918. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29122918

AMA Style

Zhou Y, Wang J, Zhang Y, Fu X, Xie H, Han J, Zhang J, Zhong J, Shan C. Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, Lyclene dharma dharma, and Their Enantiomers. Molecules. 2024; 29(12):2918. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29122918

Chicago/Turabian Style

Zhou, Yun, Jianan Wang, Yueru Zhang, Xiaochen Fu, Hongqing Xie, Jinlong Han, Jianhua Zhang, Jiangchun Zhong, and Chenggang Shan. 2024. "Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, Lyclene dharma dharma, and Their Enantiomers" Molecules 29, no. 12: 2918. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29122918

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