Highly efficient and diastereoselective synthesis of (+)-lineatin

Org Lett. 2004 Apr 29;6(9):1449-52. doi: 10.1021/ol0497032.

Abstract

[reaction: see text] A linear sequence was used to synthesize (+)-lineatin in 14 steps and 14% overall yield from a homochiral 2(5H)-furanone. Key steps of this synthetic approach feature the diastereoselective construction of a cyclobutene through a photochemical [2 + 2] cycloaddition and a regiocontrolled oxymercuration reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Molecular Conformation
  • Pheromones / chemical synthesis*
  • Pheromones / chemistry
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Sensitivity and Specificity
  • Stereoisomerism

Substances

  • Pheromones
  • Pyrans
  • lineatin