Biomimetic synthesis and structural revision of (+/-)-tridachiahydropyrone

Org Lett. 2008 Sep 18;10(18):4025-7. doi: 10.1021/ol8015836. Epub 2008 Aug 22.

Abstract

A short synthesis of the revised structure of the marine natural product tridachiahydropyrone is described. A novel biomimetic photochemical electrocyclization was employed to construct the bicyclic carbon framework from an open-chain polyene precursor. The spectroscopic data matched that of the isolated natural product, supporting a revised structure of this complex metabolite.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Biomimetics*
  • Cyclization
  • Gastropoda / chemistry
  • Photochemistry
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Pyrones
  • tridachiahydropyrone