One-Step Synthesis of Furan Rings from α-Isopropylidene Ketones Mediated by Iodine/DMSO: An Approach to Potent Bioactive Terpenes

J Org Chem. 2019 Jun 7;84(11):6886-6894. doi: 10.1021/acs.joc.9b00704. Epub 2019 May 23.

Abstract

The system I2/dimethyl sulfoxide mediates the one-step transformation of α-isopropylidene ketones into furan rings following a biomimetic approach. This methodology has been used for the synthesis of terpene furans such as mintfurane, curzerene, atractylon, and isoatractylon, all of them possessing interesting biological activities. The synthesis of linderazulene directly from 4,5-epoxygermacrone via a cascade reaction shows the potential of this protocol. Additionally, this compound proved to show significant ixodicidal activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Dimethyl Sulfoxide / chemistry*
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Iodine / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Terpenes / chemical synthesis
  • Terpenes / chemistry*

Substances

  • Alkenes
  • Furans
  • Ketones
  • Terpenes
  • Iodine
  • propylene
  • furan
  • Dimethyl Sulfoxide