Concise Synthesis of (4R,9Z)‐Octadec‐9‐en‐4‐olide, the Female Sex Pheromone of Janus integer

Medientyp: E-Artikel
Titel: Concise Synthesis of (4R,9Z)‐Octadec‐9‐en‐4‐olide, the Female Sex Pheromone of Janus integer
Beteiligte: Mori, Kenji
Erschienen: Wiley, 2005
Erschienen in: European Journal of Organic Chemistry
Sprache: Englisch
DOI: 10.1002/ejoc.200400830
ISSN: 1099-0690; 1434-193X
Schlagwörter: Organic Chemistry ; Physical and Theoretical Chemistry
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Beschreibung: <jats:title>Abstract</jats:title><jats:p>(4<jats:italic>R</jats:italic>,9<jats:italic>Z</jats:italic>)‐Octadec‐9‐en‐4‐olide, the female sex pheromone of the currant stem girdler (<jats:italic>Janus integer</jats:italic>), was synthesized in gram quantities by employing Sharpless asymmetric dihydroxylation (AD) and Jacobsen hydrolytic kinetic resolution (HKR). Crystalline (<jats:italic>R</jats:italic>)‐hexadec‐7‐yne‐1,2‐diol (87 % <jats:italic>ee</jats:italic>), obtained by AD and purified by recrystallization, was converted into (<jats:italic>R</jats:italic>)‐1,2‐epoxyhexadec‐7‐yne (87 % <jats:italic>ee</jats:italic>), which was further purified to 96 % <jats:italic>ee</jats:italic> 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)</jats:p>

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