Synthesis of Both Enantiomers of 15-Hexadecanolide, a Sex Pheromone Component of the Stink Bug, Piezodorus hybneri

Shigefumi KUWAHARA; Tomoko TSURUTA; Walter Soares LEAL; Osamu KODAMA

doi:10.1271/bbb.62.1261

Bioscience, Biotechnology, and Biochemistry

Online ISSN : 1347-6947
Print ISSN : 0916-8451

Synthesis of Both Enantiomers of 15-Hexadecanolide, a Sex Pheromone Component of the Stink Bug, Piezodorus hybneri

Shigefumi KUWAHARA, Tomoko TSURUTA, Walter Soares LEAL, Osamu KODAMA

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Keywords: 15-hexadecanolide, sex pheromone, stink bug, Piezodorus hybneri, macrolactonization

JOURNAL FREE ACCESS

1998 Volume 62 Issue 6 Pages 1261-1263

DOI https://doi.org/10.1271/bbb.62.1261

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Abstract

Both enantiomers of 15-hexadecanolide, a sex pheromone component of the stink bug (Piezodorus hybneri), were synthesized by using the Yamaguchi or Mitsunobu macrolactonization reaction of (R)-15-hydroxyhexadecanoic acid prepared from ethyl (R)-β-hydroxybutyrate in 5 steps.

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