Synthesis of the racemate of (Z)-exo-alpha-bergamotenal, a pheromone component of the white-spotted spined bug, Eysarcoris parvus Uhler

Babak Heidary Alizadeh; Shigefumi Kuwahara; Walter Soares Leal; Hong-Chao Men

doi:10.1271/bbb.66.1415

Synthesis of the racemate of (Z)-exo-alpha-bergamotenal, a pheromone component of the white-spotted spined bug, Eysarcoris parvus Uhler

Biosci Biotechnol Biochem. 2002 Jun;66(6):1415-8. doi: 10.1271/bbb.66.1415.

Authors

Babak Heidary Alizadeh¹, Shigefumi Kuwahara, Walter Soares Leal, Hong-Chao Men

Affiliation

¹ Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University, Sendai, Japan.

PMID: 12162572
DOI: 10.1271/bbb.66.1415

Abstract

The racemate of (Z)-exo-alpha-bergamotenal, a sex pheromone component of the white-spotted spined bug, was synthesized from racemic exo-alpha-bergamotene by a five-step sequence involving regioselective epoxidation and (Z)-selective Wittig olefination reactions. The 1H- and 13C-NMR spectra of the synthetic sample were identical with those of the natural material.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Insecta / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Pentanols / chemical synthesis*
Pentanols / chemistry
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry
Sex Attractants / chemical synthesis*
Sex Attractants / chemistry
Spectrophotometry, Infrared

Substances

Pentanols
Sesquiterpenes
Sex Attractants
alpha-bergamotenal