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Enantiodivergent Formal Total Synthesis of Aspercyclide C from L-(+)-Tartaric Acid

Prasad, Kavirayani R and Gandi, Vasudeva Rao and Nidhiry, John Eugene and Bhat, Kavya S (2010) Enantiodivergent Formal Total Synthesis of Aspercyclide C from L-(+)-Tartaric Acid. In: Synthesis (15). pp. 2521-2526.

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Official URL: https://www.thieme-connect.de/DOI/DOI?10.1055/s-00...

Abstract

The enantiodivergent formal syntheses of both enantiomers of aspercyclide C is accomplished. Starting from L-(+)-tartaric acid, the key protected allylic alcohol, (3R,4R)-4-(methoxy-methoxy) non-1-en-3-ol is prepared, and is then elaborated into both enantiomers of 3-(4-methoxybenzyl)oxy]non-1-en-4-ol via Mitsunobu inversion. Esterification with a known biaryl acid, followed by ring-closing metathesis and deprotection completes the syntheses.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Thieme Medical Publishers.
Keywords: Aspercyclide C; total synthesis; tartaric acid; Mitsunobu inversion; ring-closing metathesis.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 26 Oct 2010 06:59
Last Modified: 26 Oct 2010 06:59
URI: http://eprints.iisc.ernet.in/id/eprint/33402

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