In pursuit of a competitive target: total synthesis of the antibiotic kendomycin.
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.
Martin
Harry J
HJ
University of Vienna, Institute of Organic Chemistry, Waehringer Strasse 38, 1090 Wien, Austria. harry.martin@univie.ac.at
Magauer
Thomas
T
Mulzer
Johann
J
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D010084:Oxidation-Reduction; D017828:Rifabutin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D000900:Anti-Bacterial Agents; C485395:kendomycin; D017828:Rifabutin