Construction of 3,6-anhydrohexosides via intramolecular cyclization of triflates and its application to the synthesis of natural product isolated from leaves of Sauropus rostratus

Org Lett. 2014 Oct 3;16(19):5004-7. doi: 10.1021/ol5022838. Epub 2014 Sep 15.

Abstract

A novel synthetic approach to construct various 3,6-anhydrohexosides via an intramolecular cyclization of corresponding triflates is described. The nucleophilic attack from C3 p-methoxybenzylated hydroxyl to C6 trifluoromethanesulfonate on triflate structures triggered the cyclization reaction to provide 3,6-anhydrohexosides in excellent yields, making the strategy more efficient with respect to the reported protocols. By applying this methodology, a concise first total synthesis of natural product isolated from leaves of Sauropus rostratus was accomplished.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Crystallography, X-Ray
  • Cyclization
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Molecular Conformation
  • Molecular Structure
  • Phyllanthus / chemistry*
  • Plant Leaves / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Glycosides