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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

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Date

2015

Authors

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

Journal Title

Journal ISSN

Volume Title

Publisher

American Chemical Society

Abstract

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).

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Keywords

Citation

URI

http://hdl.handle.net/1885/63955

Collections

ANU Research Publications

Source

Journal of Organic Chemistry

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1021/jo5024602

Restricted until

2037-12-31

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