Synthesis of the putative structure of 15-oxopuupehenoic acid

J Org Chem. 2014 Nov 7;79(21):10689-95. doi: 10.1021/jo502048y. Epub 2014 Oct 9.

Abstract

Synthesis of the putative structure of the marine natural 15-oxopuupehenoic acid has been achieved starting from commercial (-)-sclareol. Key steps of the synthetic sequence are the Robinson annulation of a β-ketoester and methyl vinyl ketone and an unprecedented cyclization of the resulting α,β-enone, which is mediated by tin(IV) chloride in the presence of N-phenylselenophthalimide. The physical properties of the synthetic compound are somewhat different from those reported for the natural product.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemistry*
  • Cyclization
  • Diterpenes / chemistry*
  • Molecular Structure
  • Phthalimides / chemistry*
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Tin Compounds / chemistry

Substances

  • 15-oxopuupehenoic acid
  • Biological Products
  • Diterpenes
  • N-phenylselenophthalimide
  • Phthalimides
  • Sesquiterpenes
  • Tin Compounds
  • stannous chloride
  • sclareol