Asymmetric total synthesis of ent-cyclooroidin

Org Lett. 2010 Nov 5;12(21):4940-3. doi: 10.1021/ol1020916.

Abstract

An enantiospecific total synthesis of the pyrrole-imidazole natural product cyclooroidin from histidine is described. The key N1-C9 bond is constructed through an intramolecular SN2-type of reaction of a chloro ester. Subsequent imidazole azidation at the 2-position, pyrrole bromination, azide reduction, and deprotection leads to the completion of the synthesis.

Publication types

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

MeSH terms

  • Alkaloids / chemistry
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkaloids
  • Pyrroles
  • oroidin