Synthesis of tricolorin F

J Org Chem. 2004 Jul 9;69(14):4567-70. doi: 10.1021/jo030244c.

Abstract

A hetero-trisaccharide resin glycoside of jalapinolic acid known as tricolorin F has been synthesized. The approach involved the preparation of intermediate 5 and a subsequent coupling reaction with imidate 6 to produce disaccharide 7, which after deacetylation generated intermediate 8. A further coupling between this glycosyl acceptor and the quinovose glycosyl donor 9 resulted in the formation of the tricoloric acid C derivative 10. Basic hydrolysis afforded the intermediate 11, which was subsequently lactonized under Yamaguchi conditions to produce protected macrolactone 12. Removal of acetonide and benzyl protecting groups afforded pure tricolorin F (1).

Publication types

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

MeSH terms

  • Convolvulaceae / chemistry
  • Glycosides / chemical synthesis*
  • Hydrolysis
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism

Substances

  • Glycosides
  • tricolorin F