Enantioselective synthesis of $\alpha$-benzyloxy-$\omega$-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (-)-isolaurepan

Prasad, KR and Anbarasan, Pazhamalai (2007) Enantioselective synthesis of $\alpha$-benzyloxy-$\omega$-alkenals: application to the synthesis of (+)-exo-brevicomin, (+)-iso-exo-brevicomin, and (-)-isolaurepan. In: Tetrahedron-Asymmetry, 18 (12). pp. 1419-1427.

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Abstract

The enantioselective synthesis of alpha-benzyloxy aldehydes containing a terminal alkene was carried out from chiral Pool L-(+)tartaric acid by employing the stereoselective reduction of a 1,4-diketone as the key step. The synthetic utility of these aldehydes was demonstrated in the synthesis of pine beetle pheromones (+)-exo-brevicomin, (+)-iso-exo-brevicomin and a formal synthesis of 2,7cis-disubstituted oxepane (-)-isolaurepan.

Item Type:	Journal Article
Publication:	Tetrahedron-Asymmetry
Publisher:	Elsevier Science
Additional Information:	Copyright of this article belongs to Elsevier Science.
Keywords:
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	30 Apr 2009 05:41
Last Modified:	22 Feb 2019 09:29
URI:	http://eprints.iisc.ac.in/id/eprint/18558

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