Studies toward the synthesis of oximidines I and II

Org Lett. 2003 Dec 25;5(26):5019-22. doi: 10.1021/ol036007d.

Abstract

The synthesis of compound 1, a precursor for the synthesis of the oximidine II core structure 2, is described. An undesired C8-C9 isomerization occurred during the intramolecular Castro-Stephens reaction leading to macrocyle 3. The thermodynamic driving force for this unexpected isomerization was established by DFT and MP2 calculations. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkenes / chemical synthesis*
  • Indicators and Reagents
  • Lactones / chemical synthesis*
  • Molecular Conformation
  • Stereoisomerism
  • Thermodynamics

Substances

  • Alkenes
  • Indicators and Reagents
  • Lactones
  • oximidine I
  • oximidine II