K. Mori
May 1, 2005
Citations
0
Influential Citations
17
Citations
Journal
European Journal of Organic Chemistry
Abstract
(4R,9Z)-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)