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Angew Chem Int Ed Engl. 2010 Aug 2;49(33):5614-26. doi: 10.1002/anie.201000227.

In pursuit of a competitive target: total synthesis of the antibiotic kendomycin.

Author information

1
University of Vienna, Institute of Organic Chemistry, Waehringer Strasse 38, 1090 Wien, Austria. harry.martin@univie.ac.at

Abstract

Kendomycin is a novel polyketide having a unique quinone methide ansa structure and an impressive biological profile. Herein we provide a chronological overview of the synthetic work towards the title compound. Thus far, over a period of about eight years, eight groups worldwide have published on their synthetic efforts resulting in five total syntheses, one formal synthesis, and a number of fragment syntheses. Most approaches roughly mimic the biogenetic pathway, starting with an aromatic polyphenol subunit to which a polyketide chain is attached. Subsequent key steps include macrocyclization and the formation of the densely substituted tetrahydropyran ring, and then a late-stage oxidation and lactol formation.

PMID:
20818753
DOI:
10.1002/anie.201000227
[Indexed for MEDLINE]

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