Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
SYTHESIS OF OPTICALLY ACTIVE COMMON PRECURSOR OF SEX PHEROMONE OF PINE SAWFLIES: AN APPLICATION OF ENANTIOFACE-DIFFERENTIATING HYDROGENATION WITH MODIFIED NICKEL
Akira TaiMotomasa ImaidaToshihiko OdaHiroshi Watanabe
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1978 Volume 7 Issue 1 Pages 61-64

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Abstract

Synthesis of optically active 3,7-dimethylpentadecan-2-ol (1), a common precursor of sex pheromone of pine sawflies, was carried out. (+)-(2S,3S)-, (−)-(2R,3R)-, and (±)-(2R*, 3S*)-1 were prepared from (+)-(2R, 3S)-, (−)-(2S, 3R)-, and (±)-(2R*, 3S*)-3-hydroxy-2-methylbutyric acid, respectively under the conservation of their stereochemistry. Enantioface-differentiating (asymmetric) hydrogenation of methyl 2-methyl-3-oxobutyrate over tartaric acid-modified nickel catalyst gave methyl 3-hydroxy-2-methylbutyrate in high diastereomer and enantiomer excess, enabling us to obtain the optically active starting materials in high yields.

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