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

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

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.

Publication types

  • Review

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Cyclization
  • Oxidation-Reduction
  • Rifabutin / analogs & derivatives*
  • Rifabutin / chemical synthesis
  • Rifabutin / chemistry

Substances

  • Anti-Bacterial Agents
  • kendomycin
  • Rifabutin