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

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

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Abstract

Both antipodes of a-methyl-a-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.

Item Type:	Journal Article
Publication:	Tetrahedron: Asymmetry
Publisher:	Elsevier
Additional Information:	Copyright of this article belongs to Elsevier.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	07 Nov 2006
Last Modified:	19 Sep 2010 04:32
URI:	http://eprints.iisc.ac.in/id/eprint/8769

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