title: A concise asymmetric synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl Acetate and propionate, the sex pheromones of pine sawflies.
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.
authors.affiliation: Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, PR China. pqhuang@xmu.edu.cn
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
authors.forename: Hong-Qiao
authors.initials: HQ
authors.lastname: Lan
authors.forename: Xiao
authors.initials: X
authors.lastname: Zheng
authors.forename: Yuan-Ping
authors.initials: YP
authors.lastname: Ruan
mesh_terms: D000085:Acetates / Q000138:chemical synthesis*; D000473:Alkanes / Q000138:chemical synthesis*; D000818:Animals; D006927:Hymenoptera / Q000737:chemistry*; D015394:Molecular Structure; D011422:Propionates / Q000138:chemical synthesis*; D012724:Sex Attractants / Q000138:chemical synthesis*
chemical_list: C489928:(2S,3S,7S)-3,7-dimethylpentadecan-2-yl acetate; C489929:(2S,3S,7S)-3,7-dimethylpentadecan-2-yl propionate; D000085:Acetates; D000473:Alkanes; D011422:Propionates; D012724:Sex Attractants