Synthesis of (-)-ilimaquinone via a radical decarboxylation and quinone addition reaction

Org Lett. 2002 Mar 7;4(5):819-22. doi: 10.1021/ol025501z.

Abstract

[reaction: see text] A stereoselective synthesis of (-)-ilimaquinone (4) is presented. The synthetic strategy is based on a novel radical decarboxylation and quinone addition methodology that produces quinone 7 from reaction of thiohydroxamic acid derivative 8 with benzoquinone (9). Final functionalization of 7 to ilimaquinone (4) is achieved by exploring the electronic effects of the residual thiopyridyl group.

Publication types

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

MeSH terms

  • Animals
  • Anti-HIV Agents / chemical synthesis
  • Anti-Inflammatory Agents / chemical synthesis
  • Antineoplastic Agents / chemical synthesis
  • Porifera / chemistry
  • Quinones / chemical synthesis*
  • Quinones / chemistry
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism

Substances

  • Anti-HIV Agents
  • Anti-Inflammatory Agents
  • Antineoplastic Agents
  • Quinones
  • Sesquiterpenes
  • ilimaquinone