Strategies for construction of the all-carbon macrocyclic skeleton of the ansamycin antibiotic-kendomycin

Shu Xu; Hirokazu Arimoto

doi:10.1038/ja.2016.5

Strategies for construction of the all-carbon macrocyclic skeleton of the ansamycin antibiotic-kendomycin

J Antibiot (Tokyo). 2016 Apr;69(4):203-12. doi: 10.1038/ja.2016.5. Epub 2016 Feb 10.

Authors

Shu Xu^{1

2}, Hirokazu Arimoto³

Affiliations

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China.
² Department of Medicinal Chemistry, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing, China.
³ Graduate School of Life Sciences, Tohoku University, Sendai, Japan.

PMID: 26860467
DOI: 10.1038/ja.2016.5

Abstract

Kendomycin, an ansamycin-type natural product first reported in 1996, possesses a series of attractive bioactivities and a unique all-carbon macrocyclic skeleton. To the date, seven total syntheses, two formal total syntheses and a number of synthetic studies on this hot molecule have been reported. In this short review article, we mainly survey and comment on these efforts regarding the difficult macrocyclization strategies.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Antineoplastic Agents / chemical synthesis*
Humans
Lactams, Macrocyclic / chemical synthesis*
Rifabutin / analogs & derivatives*
Rifabutin / chemical synthesis
Streptomyces / metabolism
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Antineoplastic Agents
Lactams, Macrocyclic
kendomycin
Rifabutin