Synthesis of the Spirocyclic Framework of Sesterterpenoid Natural Products

J Org Chem. 2015 Mar 6;80(5):2715-23. doi: 10.1021/jo502897u. Epub 2015 Feb 18.

Abstract

A convergent synthetic route to the sesterterpenoid framework of the bioactive phorbaketal and alotaketal natural product families has been established. The synthetic approach hinges on a Hosomi-Sakurai coupling of complex acetal and allylsilane coupling partners, followed by DDQ-promoted oxidative cyclization of highly unsaturated advanced intermediates. This robust synthetic approach enables further investigations into the members of these natural product families and readily provides access to analogues for biological testing.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Phenomena
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Cyclization
  • Molecular Structure
  • Oxidation-Reduction
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry

Substances

  • Biological Products
  • Spiro Compounds
  • Terpenes