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Total Syntheses of the Resorcylic Acid Lactone Neocosmosin A and Its Enantiomer

Zhang, Yiwen; Dlugosch, Michael; Jubermann, Martin; Banwell, Martin; Ward, James

Description

A total synthesis of the structure, 1, assigned to the recently reported resorcylic acid lactone (RAL) neocosmosin A has been established. Olefin-cross metathesis, ring-closing metathesis, palladium-catalyzed Meinwald rearrangement, and Mitsunobu esterification reactions were used as key steps. A late-stage and simple modification to the reaction sequence also provided compound ent-1 that, in fact, represents the true structure of the natural product.

CollectionsANU Research Publications
Date published: 2015
Type: Journal article
URI: http://hdl.handle.net/1885/63651
Source: Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b00590

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