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American Chemical Society, Journal of Organic Chemistry, 11(69), p. 3964-3967, 2004

DOI: 10.1021/jo0497961

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A concise asymmetric synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate and propionate, the sex pheromones of pine sawflies

Journal article published in 2004 by Zheng,X, 黄培强, 郑啸, Pq-Q. Huang ORCID, Huang,PQ, Hq-Q. Lan, Roan,YP, Xiao Zheng, Lan,HQ, Yp Roan, Yuan-Ping Ruan
This paper was not found in any repository; the policy of its publisher is unknown or unclear.
This paper was not found in any repository; the policy of its publisher is unknown or unclear.

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Abstract

(2S,3S,7S)-3,7-Dimethylpentadecan-2-yl acetate (2) and its propionate analogue (3) are the main sex pheromones of all Neodiprion species and Diprion similes, respectively. Starting from (S)-malic acid and employing a highly chemo-, regio-, and stereoselective tandem ester reduction-epoxide formation-reductive epoxide-opening reaction protocol, an efficient total synthesis of (2S,3S,7S)-2 and -3 is reported herein.