Synthetic studies on polymaxenolides: synthesis and structure elucidation of nominal epoxyafricanane and other africane-type sesquiterpenoids

J Org Chem. 2011 Aug 5;76(15):6258-63. doi: 10.1021/jo2010186. Epub 2011 Jul 6.

Abstract

A racemic total synthesis of the sesquiterpenoid unit of the hybrid marine natural product polymaxenolide has been achieved based on a three-component assembly followed by ring-closing metathesis as the key steps. However, the spectral data of our product synthesized from Δ(9(15))-africanene by epoxidation were not identical with those of the natural product named epoxyafricanane. The structure confirmation of the synthetic nominal epoxyafricanane is described.

MeSH terms

  • Biological Products
  • Cyclization
  • Marine Toxins / chemistry*
  • Molecular Structure
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry*

Substances

  • Biological Products
  • Marine Toxins
  • Sesquiterpenes
  • Terpenes
  • africanene
  • epoxyafricanane