Modular total syntheses of the marine-derived resorcylic Acid lactones cochliomycins a and B using a late-stage nozaki-hiyama-kishi macrocyclization reaction

Benoit Bolte; Jose A Basutto; Christopher S Bryan; Mary J Garson; Martin G Banwell; Jas S Ward

doi:10.1021/jo5024602

Modular total syntheses of the marine-derived resorcylic Acid lactones cochliomycins a and B using a late-stage nozaki-hiyama-kishi macrocyclization reaction

J Org Chem. 2015 Jan 2;80(1):460-70. doi: 10.1021/jo5024602. Epub 2014 Nov 26.

Authors

Benoit Bolte¹, Jose A Basutto¹, Christopher S Bryan¹, Mary J Garson², Martin G Banwell¹, Jas S Ward¹

Affiliations

¹ †Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 2601, Australia.
² ‡School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane QLD 4072, Australia.

PMID: 25405580
DOI: 10.1021/jo5024602

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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ascomycota / chemistry*
Cyclization
Hydroxybenzoates / chemical synthesis*
Hydroxybenzoates / chemistry
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Conformation

Substances

Hydroxybenzoates
Lactones
cochliomycin A
cochliomycin B