An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth, has been achieved efficiently. From a key intermediate (R)-4-(benzyloxy)-2-methylbutan-1-ol and 1,11-undecanediol, the target molecule was synthesized in 10 linear steps with 34% yield. The key intermediate (R)-4-benzyloxy-2-methylbutan-1-ol was prepared through Evans′ template (R)-4-benzyl-2-oxazolidinone, namely (R)-4-benzyl-2-oxazolidinone in 98% e.e. 1,11-Undecanediol was selectively benzylated, iodinated, and then transformed into a phosphonium salt. After a Wittig reaction, the carbon skeleton was constructed. After the requisite functional group interconversions, the (S)-14-methyl-1-octadecene was smoothly obtained. The characteristic of our synthesis lies in that it is a chiral-pool strategy and a very convenient chemical process.
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ACKNOWLEDGMENT
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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Published in Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2022, pp. 276–280.
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He, GG., He, CT., Rao, BQ. et al. Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth. Chem Nat Compd 58, 320–325 (2022). https://doi.org/10.1007/s10600-022-03668-z
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DOI: https://doi.org/10.1007/s10600-022-03668-z