One-pot synthesis of hollongdione from dipterocarpol

Nat Prod Commun. 2014 Oct;9(10):1417-20.

Abstract

A one-pot synthesis of a hybrid triterpenoid-steroid molecule, hollongdione (22,23,24,25,26,27-hexanordammar-3,20-dion), was achieved in a yield of 89%, based on the selective dehydration of dipterocarpol following ozonolysis. The structure of hollongdione was confirmed by X-ray analysis for the first time. Dammar-20(22),24(25)-dien inhibited the growth of Mycobacterium tuberculosis (strain H37Rv) in vitro with a MIC of 50 μg/mL.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology
  • Microbial Sensitivity Tests
  • Mycobacterium tuberculosis / drug effects*
  • Steroids / chemistry*
  • Triterpenes / chemistry*

Substances

  • Antitubercular Agents
  • Steroids
  • Triterpenes