A concise asymmetric synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl Acetate and propionate, the sex pheromones of pine sawflies.
(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.
Huang
Pei-Qiang
PQ
Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, PR China. pqhuang@xmu.edu.cn
Lan
Hong-Qiao
HQ
Zheng
Xiao
X
Ruan
Yuan-Ping
YP
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*
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