Gold catalysis: regio- and stereoselective total synthesis of xyloketals D and G and the related natural product alboatrin

J Org Chem. 2013 Mar 15;78(6):2413-21. doi: 10.1021/jo302545n. Epub 2013 Mar 6.

Abstract

A new and efficient one-pot desilylation-gold-catalyzed cycloisomerization of alkynes containing a silyl-protected phenolic -OH and a free alcoholic -OH unit leads selectively to the formation of tetrahydrofuranobenzopyran ring system. This approach has been used for the regio- and stereoselective synthesis of xyloketal D, xyloketal G, and the related natural product alboatrin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Gold / chemistry*
  • Molecular Structure
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Quinones / chemical synthesis*
  • Quinones / chemistry
  • Stereoisomerism

Substances

  • Pyrans
  • Quinones
  • alboatrin
  • xyloketal D
  • xyloketal G
  • Gold