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Concise Synthesis of (4 R ,9 Z )‐Octadec‐9‐en‐4‐olide, the Female Sex Pheromone of Janus integer
Author(s) -
Mori Kenji
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400830
Subject(s) - chemistry , stereochemistry , sharpless asymmetric dihydroxylation , kinetic resolution , epoxide , lactone , dihydroxylation , diol , yield (engineering) , epoxide hydrolase , total synthesis , stereoselectivity , enantioselective synthesis , organic chemistry , enzyme , materials science , microsome , metallurgy , catalysis
(4 R ,9 Z )‐Octadec‐9‐en‐4‐olide, the female sex pheromone of the currant stem girdler ( Janus integer ), was synthesized in gram quantities by employing Sharpless asymmetric dihydroxylation (AD) and Jacobsen hydrolytic kinetic resolution (HKR). Crystalline ( R )‐hexadec‐7‐yne‐1,2‐diol (87 % ee ), obtained by AD and purified by recrystallization, was converted into ( R )‐1,2‐epoxyhexadec‐7‐yne (87 % ee ), which was further purified to 96 % ee by HKR. The epoxide was converted into the target lactone in 14 % overall yield based on hex‐5‐en‐1‐ol (11 steps). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)