Stereoselective Synthesis of erythro-Serricornin, (4R, 6R, 7S)-, and (4596R, 75')-4?6-Dimethyl-7-hydroxynonan-3-one9 Stereoisomers of the Sex Pheromone of Cigarette Beetle

Tatsuji Chuman; Masahiro Kohno; Kunio Kato; Masao Noguchi; Hiroko Nomi; Kenji Mori

doi:10.1271/bbb1961.45.2019

Agricultural and Biological Chemistry

Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369

Stereoselective Synthesis of erythro-Serricornin, (4R, 6R, 7S)-, and (4596R, 75')-4?6-Dimethyl-7-hydroxynonan-3-one9 Stereoisomers of the Sex Pheromone of Cigarette Beetle

Tatsuji Chuman, Masahiro Kohno, Kunio Kato, Masao Noguchi, Hiroko Nomi, Kenji Mori

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1981 Volume 45 Issue 9 Pages 2019-2023

DOI https://doi.org/10.1271/bbb1961.45.2019

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Abstract

A stereoselective synthesis of erythro-serricornin [(4RS, 6R, 7S)-4, 6-dimethyl-7-hydroxynonan-3-one] was completed starting from L-(+)-tartaric acid. The relative configuration of C(6)-methyl and C(7)-hydroxyl groups in naturally occurring serricornin was threo.

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