Concise enantioselective construction of a bridged azatricyclic framework via domino semipinacol-Schmidt reaction

Chem Commun (Camb). 2012 Jun 11;48(46):5778-80. doi: 10.1039/c2cc31906c. Epub 2012 May 2.

Abstract

A TiCl(4)-promoted domino semipinacol-Schmidt reaction of oxaspiropentane-azide provides an easy access to bridged azatricyclic ring systems, which possess the azaquaternary center, present in the immunosupressant FR901483 and platelet aggregation inhibitor daphlongeranine B.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Aza Compounds / chemistry*
  • Azides / chemistry
  • Crystallography, X-Ray
  • Cyclohexenes / chemistry*
  • Molecular Conformation
  • Organophosphorus Compounds / chemistry
  • Platelet Aggregation Inhibitors / chemistry
  • Stereoisomerism
  • Titanium / chemistry*

Substances

  • Alkaloids
  • Aza Compounds
  • Azides
  • Cyclohexenes
  • FR 901483
  • Organophosphorus Compounds
  • Platelet Aggregation Inhibitors
  • daphlongeranine B
  • semipinacol
  • titanium tetrachloride
  • Titanium