Asymmetric total synthesis of (+)-K01-0509 B: determination of absolute configuration

Org Lett. 2006 Nov 23;8(24):5577-80. doi: 10.1021/ol062282z.

Abstract

K01-0509 B is a novel natural product which contains a carbamoylated cyclic guanidine. Our asymmetric total synthesis features a Sharpless asymmetric epoxidation and a stereocontrolled construction of the cyclic guanidine via an asymmetric nitroaldol reaction, followed by intramolecular SN2 cyclization. These reactions allowed the cyclic guanidine and the adjacent hydroxy group to be assembled, facilitating the asymmetric total synthesis and determination of the absolute stereochemistry of K01-0509 B. [reaction: see text].

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Catalysis
  • Cobalt / chemistry
  • Cyclization
  • Epoxy Compounds / chemical synthesis
  • Ethanolamines
  • Guanidines / chemical synthesis*
  • Guanidines / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Stereoisomerism
  • Streptomyces / chemistry
  • Streptomyces / metabolism

Substances

  • Anti-Bacterial Agents
  • Epoxy Compounds
  • Ethanolamines
  • Guanidines
  • K01-0509 B
  • Cobalt
  • RP333