Synthesis of the tetracyclic core of berkelic acid using gold(I)-catalyzed hydroarylation and oxidative radical cyclizations

Org Lett. 2012 Dec 7;14(23):5820-3. doi: 10.1021/ol302536j. Epub 2012 Nov 27.

Abstract

A synthetic approach to the tetracyclic core of berkelic acid is reported using gold(I)-catalyzed intramolecular hydroarylation and oxidative radical cyclizations to effect the key ring-forming steps. The carboxylic acid was introduced via a late-stage palladium-catalyzed carbonylation to afford the core tetracycle with the correct relative stereochemistry for the natural product.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Gold / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Spiro Compounds
  • berkelic acid
  • Gold