Synthesis of the branched C-glycoside substructure of altromycin B

Org Lett. 2005 Aug 18;7(17):3621-4. doi: 10.1021/ol050975u.

Abstract

Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b). [reaction: see text]

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.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aminoglycosides / chemical synthesis*
  • Aminoglycosides / chemistry*
  • Catalysis
  • Molecular Structure
  • Stereoisomerism
  • Tungsten / chemistry

Substances

  • Aminoglycosides
  • altromycin B
  • Tungsten