Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide

Org Lett. 2002 Aug 22;4(17):3009-11. doi: 10.1021/ol026467r.

Abstract

[reaction: see text] A study toward a possible biomimetic hetero Diels-Alder reaction is reported between humulene and a novel tropolone ortho-quinone methide. A suitable tropolone ortho-quinone methide precursor has been prepared from 3-methyl-2-furoate. Heating the ortho-quinone methide precursor gave a tropolone ortho-quinone methide, which in the presence of humulene underwent a hetero Diels-Alder reaction to give a deoxy analogue of epolone B.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anemia / drug therapy
  • Erythropoietin / genetics
  • Gene Expression / drug effects
  • Indolequinones*
  • Indoles / chemistry
  • Molecular Mimicry
  • Monocyclic Sesquiterpenes
  • Quinones / chemistry
  • Sesquiterpenes / chemistry
  • Tropolone / analogs & derivatives*
  • Tropolone / chemical synthesis
  • Tropolone / pharmacology

Substances

  • Indolequinones
  • Indoles
  • Monocyclic Sesquiterpenes
  • Quinones
  • Sesquiterpenes
  • Erythropoietin
  • quinone methide
  • humulene
  • Tropolone