Efficient generation of ortho-quinone methide: application to the biomimetic syntheses of (±)-schefflone and tocopherol trimers

Org Lett. 2012 Jan 6;14(1):18-21. doi: 10.1021/ol202641y. Epub 2011 Nov 2.

Abstract

An efficient method using silver oxide-mediated oxidation for the synthesis of ortho-quinone methides has been developed and applied to the biomimetic syntheses of novel trimeric natural products, (±)-schefflone and tocopherol trimers. Further studies of the critical trimerization as well as substrate scope and limitations are also reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biomimetic Materials / chemical synthesis*
  • Indolequinones / chemistry*
  • Molecular Structure
  • Monoterpenes / chemistry*
  • Oxidation-Reduction
  • Tocopherols / chemistry*

Substances

  • Indolequinones
  • Monoterpenes
  • schefflone
  • quinone methide
  • Tocopherols