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.

PDF total.pdf - Published Version Restricted to Registered users only Download (130kB) | Request a copy

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
Publication:	Synthesis
Publisher:	Thieme Medical Publishers
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.ac.in/id/eprint/33402

Actions (login required)

View Item