Total synthesis of (+/-)-alpha- and beta-lycoranes by sequential chemoselective conjugate addition-stereoselective nitro-Michael cyclization of an omega-nitro-alpha,beta,psi,omega-unsaturated ester

Org Lett. 2003 Apr 3;5(7):1123-6. doi: 10.1021/ol0341905.

Abstract

[reaction: see text] An omega-nitro-alpha,beta,psi,omega-unsaturated ester underwent a chemoselective conjugate addition of a nitroolefin moiety with aryllithium to produce a psi-aryl-omega-nitro-alpha,beta-unsaturated ester, which was then stereoselectively cyclized by intramolecular nitro-Michael reaction giving a functionalized cyclohexane applicable to the total synthesis of (+/-)-alpha- and beta-lycoranes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Amaryllidaceae Alkaloids*
  • Cyclization
  • Esters / chemistry*
  • Molecular Structure
  • Nitrogen / chemistry
  • Stereoisomerism

Substances

  • Alkaloids
  • Amaryllidaceae Alkaloids
  • Esters
  • lycorane
  • Nitrogen