Abstract
Based on the previously synthesized chiral intermediate, a new synthesis of pine sawfly pheromones bearing 3 stereocenters has been achieved. The key steps were Evans’ template induction, Wittig olefination, and conventional chemical operations. (2S,3S,7S)-3,7-Dimethylpentadecan-2-yl acetate and propanoate were obtained in 9 steps with an overall yield of 34%.
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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 NSFC grants nos. 31301712 and 31760639. Partial financial support from the Jiangxi Technological Normal University is greatly appreciated. Zhen-Ting Du thanks Opening Funds of the 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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He, GG., Yang, X., Cheng, Y. et al. New Synthesis of Pine Sawfly Pheromones. Russ J Org Chem 58, 1311–1318 (2022). https://doi.org/10.1134/S1070428022090172
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DOI: https://doi.org/10.1134/S1070428022090172