Total Synthesis of the Plant Growth Promoter Auxofuran Featuring a Gold(I) Catalyzed Furan Formation

J Org Chem. 2020 Jun 19;85(12):8203-8208. doi: 10.1021/acs.joc.0c00408. Epub 2020 Jun 4.

Abstract

A concise synthesis of auxofuran (1) was developed. Starting with a Sonogashira cross-coupling reaction, enynol (10) was prepared. A gold(I) catalyzed cycloisomerization led to disubstituted furan 12. Via an intramolecular Friedel-Crafts cyclization, a dihydrobenzofuranone was obtained. Functional group manipulations, including benzylic oxidation, led to the target molecule.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans
  • Catalysis
  • Cyclization
  • Furans*
  • Gold*
  • Molecular Structure

Substances

  • Benzofurans
  • Furans
  • auxofuran
  • Gold