Xanthone natural products via N-heterocyclic carbene catalysis: total synthesis of atroviridin

J Org Chem. 2011 May 20;76(10):3960-7. doi: 10.1021/jo200303c. Epub 2011 Apr 18.

Abstract

The total synthesis of atroviridin has been accomplished by a linear route involving the N-heterocyclic carbene (NHC)-catalyzed aroylation of the fluorobenzene derivative, Claisen cyclization of the O-propargylated benzophenones, and intramolecular 1,4-addition of the quinone intermediates. The result provides a viable route to xanthone natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoquinones / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Catalysis
  • Heterocyclic Compounds / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Xanthones / chemical synthesis*
  • Xanthones / chemistry

Substances

  • Benzoquinones
  • Biological Products
  • Heterocyclic Compounds
  • Xanthones
  • atroviridin
  • carbene
  • quinone
  • Methane