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Synthesis of All Four Stereoisomers of 6,10,13‐Trimethyltetradecan‐2‐one, a Sex Pheromone Component Produced by Males of the Stink Bug Pallantia macunaima
Author(s) -
Muraki Yuta,
Taguri Tomonori,
Yamamoto Masanobu,
Zarbin Paulo H. G.,
Ando Tetsu
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201688
Subject(s) - pentatomidae , heteroptera , stereospecificity , chemistry , sex pheromone , enantiomer , pheromone , stereochemistry , pest analysis , botany , organic chemistry , biology , catalysis
The stink bug Pallantia macunaima (Heteroptera: Pentatomidae) is a soybean pest in southern Brazil, and the males produce 6,10,13‐trimethyltetradecan‐2‐one to communicate with females. All four stereoisomers of the sex pheromone were synthesized by coupling two chiral building blocks, which were synthesized from ( S )‐ and ( R )‐propylene oxides using stereospecific inversion of secondary tosylates as a key reaction. The enantiomeric purities of the building blocks were confirmed by chiral HPLC analysis.