1978 Volume 7 Issue 1 Pages 61-64
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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