Yamaguchi-type lactonization as a key step in the synthesis of marine metabolites: (+)-luffalactone

J Org Chem. 2009 Oct 16;74(20):7750-4. doi: 10.1021/jo9013996.

Abstract

A Yamaguchi-type cyclization of 5 and subsequent photochemical oxidation of the furanic ring are the key steps in the first synthesis of the marine metabolite (+)-luffalactone 4 and its epimer at C-16, 16-epi-luffalactone, 27. With this work, we have successfully established the absolute configuration of the natural product. The key intermediate 5 was obtained from the easily accessible diacetate 6a/6b.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Heterocyclic Compounds, 3-Ring / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Photochemistry*

Substances

  • Heterocyclic Compounds, 3-Ring
  • Lactones
  • luffalactone