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Modular total syntheses of the marine-derived resorcylic acid lactones cochliomycins A and B using a late-stage Nozaki-Hiyama-Kishi macrocyclization reaction

Bolte, Benoit; Basutto, Jose; Bryan, Christopher; Garson, Mary J; Banwell, Martin; Ward, James


The natural products cochliomycin A (1) and cochliomycin B (2), two resorcylic acid lactones obtained from marine sources, have been prepared in a concise and stereocontrolled manner from the readily accessible building blocks 4-6. Olefin cross-metathesis, trans-esterification and Nozaki-Hiyama-Kishi (NHK) macrocyclization reactions were employed in the key steps. Hydrolysis of the immediate precursor to cochliomycin B affords the resorcylic acid lactone zeaenol (24).

CollectionsANU Research Publications
Date published: 2015
Type: Journal article
Source: Journal of Organic Chemistry
DOI: 10.1021/jo5024602


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