Regiocontrolled synthesis of the trimeric quinone framework of conocurvone

Org Lett. 2002 Feb 21;4(4):521-4. doi: 10.1021/ol010272m.

Abstract

[reaction: see text] The trimeric quinone framework of conocurvone is crucial for its potent anti-HIV activity. A new synthesis of trimeric quinones based on stepwise substitution of the halogens in 2,3-dihaloquinones by hydroxyquinone anions is described. Chlorinated biquinones are key intermediates that undergo regiospecific substitution reactions to yield trimeric quinone monomethyl ethers.

Publication types

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

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Filtration
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / chemistry
  • Quinones / chemical synthesis*
  • Quinones / chemistry
  • Stereoisomerism

Substances

  • Anti-HIV Agents
  • Indicators and Reagents
  • Naphthoquinones
  • Quinones
  • conocurvone