Modular, Scalable Synthesis of Group A Streptogramin Antibiotics

J Am Chem Soc. 2017 Sep 27;139(38):13304-13307. doi: 10.1021/jacs.7b08577. Epub 2017 Sep 18.

Abstract

Streptogramin antibiotics are used clinically to treat multidrug-resistant bacterial infections, but their poor physicochemical properties and narrow spectra of activity have limited their utility. New methods to chemically modify streptogramins would enable structural optimization to overcome these limitations as well as to combat growing resistance to the class. Here we report a modular, scalable synthesis of group A streptogramin antibiotics that proceeds in 6-8 linear steps from simple chemical building blocks. We have applied our route to the synthesis of four natural products in this class including two that have never before been accessed by fully synthetic routes. We anticipate that this work will lead to the discovery of new streptogramin antibiotics that overcome previous limitations of the class.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Molecular Structure
  • Streptogramin Group A / chemical synthesis*
  • Streptogramin Group A / chemistry
  • Virginiamycin / chemical synthesis
  • Virginiamycin / chemistry

Substances

  • Anti-Bacterial Agents
  • Biological Products
  • Streptogramin Group A
  • Virginiamycin