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In Pursuit of a Competitive Target: Total Synthesis of the Antibiotic Kendomycin
Author(s) -
Martin Harry J.,
Magauer Thomas,
Mulzer Johann
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201000227
Subject(s) - polyketide , total synthesis , tetrahydropyran , stereochemistry , chemistry , ring (chemistry) , lactol , combinatorial chemistry , lactone , biochemistry , biosynthesis , organic chemistry , enzyme
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.