Abstract
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)
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