An efficient method for the synthesis of enol ethers and enecarbamates. Total syntheses of isoindolobenzazepine alkaloids, lennoxamine and chilenine

Org Biomol Chem. 2007 Jun 21;5(12):1849-53. doi: 10.1039/b706087d. Epub 2007 May 16.

Abstract

An efficient method for the synthesis of enol ethers and enecarbamates has been developed based on catalytic hydrosilane reduction of alpha-phosphonoxy enol ethers and alpha-phosphonoxy enecarbamates. This method has been applied to the total syntheses of two isoindolobenzazepine alkaloids, lennoxamine and chilenine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Benzazepines / chemical synthesis*
  • Benzazepines / chemistry
  • Carbamates / chemical synthesis*
  • Carbamates / chemistry
  • Cyclization
  • Dioxanes / chemical synthesis*
  • Dioxanes / chemistry
  • Ethers, Cyclic / chemical synthesis*
  • Ethers, Cyclic / chemistry
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Alkaloids
  • Alkenes
  • Benzazepines
  • Carbamates
  • Dioxanes
  • Ethers, Cyclic
  • Heterocyclic Compounds
  • Indoles
  • chilenine
  • lennoxamine