Synthesis of nitrogen-functionalized cyclohexanes using chemoselective conjugate addition of phenyllithium to linear omega-nitro-alpha,beta,psi,omega-unsaturated ester and subsequent stereoselective intramolecular nitro-Michael cyclization

Chem Pharm Bull (Tokyo). 2004 Sep;52(9):1109-13. doi: 10.1248/cpb.52.1109.

Abstract

Nitrogen-functionalized cyclohexane derivatives with three contiguous chiral centers were synthesized by nitroalkene-selective conjugate addition of phenyllithium to a omega-nitro-alpha,beta,psi,omega-unsaturated ester and subsequent stereocontrolled intramolecular nitro-Michael cyclization with cesium fluoride and a quaternary ammonium bromide. The cyclohexanes were applicable to the total synthesis of alpha-, beta- and gamma-lycoranes.

MeSH terms

  • Cyclization
  • Cyclohexanes / chemical synthesis*
  • Esters / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Nitrogen / chemistry*
  • Organometallic Compounds / chemistry*

Substances

  • Cyclohexanes
  • Esters
  • Organometallic Compounds
  • phenyllithium
  • Nitrogen