Short and efficient synthetic route to methyl α-trioxacarcinoside B and anomerically activated derivatives

Org Lett. 2011 Oct 21;13(20):5584-7. doi: 10.1021/ol202315m. Epub 2011 Sep 29.

Abstract

A 9-step synthetic route to the complex carbohydrate methyl α-trioxacarcinoside B from 2-acetylfuran is described. Anomerically activated forms, including 1-phenylthio, 1-O-(4'-pentenyl), 1-fluoro, and 1-O-acetyl derivatives are also prepared.

Publication types

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

MeSH terms

  • Furans / chemistry*
  • Molecular Structure
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / chemistry
  • Stereoisomerism

Substances

  • Furans
  • Monosaccharides
  • methyl alpha-trioxacarcinoside B
  • 2-acetylfuran