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J Org Chem

Title:		"A concise asymmetric synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl Acetate and propionate, the sex pheromones of pine sawflies"
Author(s):		Huang PQ; Lan HQ; Zheng X; Ruan YP;
Address:		"Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, PR China. pqhuang@xmu.edu.cn"
Journal Title:		J Org Chem
Year:		2004
Volume:		69
Issue:		11
Page Number:		3964 - 3967
DOI:		10.1021/jo0497961
ISSN/ISBN:		0022-3263 (Print) 0022-3263 (Linking)
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"
Keywords:		Acetates/*chemical synthesis Alkanes/*chemical synthesis Animals Hymenoptera/*chemistry Molecular Structure Propionates/*chemical synthesis Sex Attractants/*chemical synthesis;
Notes:		"MedlineHuang, Pei-Qiang Lan, Hong-Qiao Zheng, Xiao Ruan, Yuan-Ping eng Research Support, Non-U.S. Gov't 2004/05/22 J Org Chem. 2004 May 28; 69(11):3964-7. doi: 10.1021/jo0497961"