Asymmetric synthesis of both enantiomers of α-methyl-α-methoxyphenylacetic acid from L-(+)-tartaric acid: formal enantioselective synthesis of insect pheromone (-)-frontalin

Prasad, Kavirayani R. ; Chandrakumar, Appayee ; Anbarasan, Pazhamalai (2006) Asymmetric synthesis of both enantiomers of α-methyl-α-methoxyphenylacetic acid from L-(+)-tartaric acid: formal enantioselective synthesis of insect pheromone (-)-frontalin Tetrahedron: Asymmetry, 17 (13). pp. 1979-1984. ISSN 0957-4166

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetasy.2006.07.007

Abstract

Both antipodes of α-methyl-α-methoxyarylacetic acid derivatives were prepared from a common chiralpool precursor L-(+)-tartaric acid. The key step involves the addition of Grignard reagents to 1,4-diketones derived from tartaric acid. The utility of this strategy was applied in the formal enantioselective synthesis of pine beetle pheromone (−)-frontalin.

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