Synthesis of a novel polyhydroxylated salicylic acid lactone framework

Org Lett. 2009 Feb 19;11(4):871-4. doi: 10.1021/ol802852r.

Abstract

The facile preparation of a novel 8-membered polyhydroxylated salicylic acid lactone from 2,6-dihydroxybenzoic acid and sodium thio-D-glucose is described. The key step involved a sodium hydride promoted intramolecular lactonization in the presence of excess TMSCl, which led to isolation of the "natural product like" lactone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Glucose / analogs & derivatives
  • Glucose / chemistry
  • Hydroxybenzoates / chemistry
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification
  • Indole Alkaloids / pharmacology
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Salicylates / chemical synthesis*
  • Salicylates / chemistry
  • Sodium Compounds / chemistry
  • Stereoisomerism

Substances

  • Hydroxybenzoates
  • Indole Alkaloids
  • Lactones
  • Salicylates
  • Sodium Compounds
  • ovatolide
  • sodium hydride
  • Glucose
  • gamma-resorcylic acid