Asymmetric synthesis and absolute configuration of streptophenazine G

J Org Chem. 2012 Apr 6;77(7):3191-6. doi: 10.1021/jo202642a. Epub 2012 Mar 21.

Abstract

The asymmetric synthesis of the antibacterial natural product, streptophenazine G, has been achieved by employing asymmetric alkylation and asymmetric aldol reactions using chiral oxazolidinones as the key steps. The originally proposed structure for streptophenazine G has been revised, and its absolute configuration has been determined to be 1'S,2'R,6'S. The asymmetric total synthesis of 6'-epi-streptophenazine G is also described.

MeSH terms

  • Alkylation
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry*
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry*
  • Molecular Structure
  • Phenazines / chemical synthesis*
  • Phenazines / chemistry*
  • Stereoisomerism
  • Streptomyces / chemistry*

Substances

  • Anti-Bacterial Agents
  • Biological Products
  • Phenazines
  • streptophenazine G