Synthesis of the carboline disaccharide domain of shishijimicin A

Org Lett. 2011 Aug 5;13(15):3924-7. doi: 10.1021/ol201444t. Epub 2011 Jun 28.

Abstract

A synthetic route to the carboline disaccharide domain (2) of shishijimicin A (1) has been developed. The convergent synthesis relies on a novel application of the Reetz-Müller-Starke reaction to form the central, sulfur-bearing quaternary carbon center and addition of the carboline structural motif as a dianion to a disaccharide aldehyde fragment.

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

  • Carbolines / chemistry*
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Enediynes / chemistry*
  • Fluorides / chemistry
  • Molecular Structure

Substances

  • Carbolines
  • Disaccharides
  • Enediynes
  • Shishijimicin A
  • Fluorides