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Asymmetric Synthesis of (+)-Tanikolide and the β-Methyl-Substituted Analogues of (+)-Tanikolide and (–)-Malyngolide

✍ Scribed by Robert Doran; Lesley Duggan; Surrendra Singh; Colm D. Duffy; Patrick J. Guiry

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 770 KB
Volume: 2011
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201101190

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✦ Synopsis

Abstract

The δ‐lactone‐containing natural product (+)‐tanikolide, a brine shrimp toxin and antifungal compound, was synthesized in nine steps with an overall yield of 26.4 % by employing Sharpless asymmetric epoxidation and ZrCl~4~‐catalyzed intramolecular acetalization as the key steps. The novel β‐methyl‐substituted analogues of (+)‐tanikolide and(–)‐malyngolide have also been prepared by using the same asymmetric synthetic approach.

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## Abstract For Abstract see ChemInform Abstract in Full Text.

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