Efficient access to 2-isobetulinic acid, 2-isooleanolic acid, and 2-isoursolic acid

J Org Chem. 2008 Sep 19;73(18):7405-8. doi: 10.1021/jo801232s. Epub 2008 Aug 19.

Abstract

An efficient access to 2-isobetulin, 2-isobetulinic acid, 2-isooleanolic acid, and 2-isoursolic acid has been developed. The key step is a novel one-pot conversion of 2,3-dihydroxy triterpenes to 3-deoxy-2-oxo triterpenes. This method provides a new access to 3-deoxy-2-substituted pentacyclic triterpenes as potential therapeutic agents against metabolic diseases, tumors, and HIV infection.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Betulinic Acid
  • Molecular Conformation
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemical synthesis*
  • Oleanolic Acid / chemistry
  • Pentacyclic Triterpenes
  • Stereoisomerism
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry*
  • Ursolic Acid

Substances

  • Pentacyclic Triterpenes
  • Triterpenes
  • Oleanolic Acid
  • Betulinic Acid