Tetrahedron: Asymmetry

Stereoselective synthesis of (2S, 3S, 7S)-3, 7-dimethylpentadecan-2-ol and its propionate, the sex pheromones of pine sawflies

V Kovalenko, E Matiushenkov

Index: Kovalenko, Vitaly; Matiushenkov, Evgenii Tetrahedron: Asymmetry, 2012 , vol. 23, # 18-19 p. 1393 - 1399,7

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Citation Number: 4

Abstract

The stereoselective synthesis of (2S, 3S, 7S)-3, 7-dimethylpentadecan-2-ol (diprionol) and its propionate, the sex pheromones of pine sawflies (Neodiprion sp. and other), in high enantiomeric purity was achieved from (1R, 3S)-2, 2-dichloro-3- methylcyclopropanecarboxylic acid. The carbon skeleton of diprionol was formed via copper- catalyzed cross-coupling reactions and diastereoselective methylation of the intermediate ...