A Flexible Asymmetric Synthesis of the Tetracyclic Core of Berkelic Acid Using a Horner-Wadsworth-Emmons/oxa-Michael Cascade

Org Biomol Chem. 2010 Mar 21;8(6):1284-6. doi: 10.1039/b927219b. Epub 2010 Jan 26.

Abstract

The one-pot Horner-Wadsworth-Emmons/oxa-Michael cascade followed by spiroketalisation affords the tetracyclic benzannulated spiroketal core of berkelic acid, an extremophile natural product with selective activity against ovarian cancer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Spiro Compounds
  • berkelic acid