Synthesis of two conformationally constrained analogues of the minor tobacco alkaloid anabasine

Org Lett. 2000 Jul 27;2(15):2291-3. doi: 10.1021/ol006056f.

Abstract

The anabasine analogues spiro[4-azaindan-1,2'-piperidine] (7) and spiro[6-azaindan-1,2'-piperidine] (8) have been prepared. A series of palladium-catalyzed reactions, where an intramolecular cyclization constituted a key reaction, were utilized for the preparation of the two target compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Alkaloids / metabolism
  • Anabasine / analogs & derivatives*
  • Anabasine / chemical synthesis*
  • Anabasine / chemistry
  • Anabasine / metabolism
  • Catalysis
  • Cyclization
  • Nicotiana / chemistry*
  • Nicotine / analogs & derivatives
  • Nicotine / chemical synthesis
  • Nicotine / chemistry
  • Nicotine / metabolism
  • Palladium / metabolism
  • Piperidines / chemical synthesis*
  • Piperidines / chemistry
  • Piperidines / metabolism
  • Plants, Toxic*
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry
  • Spiro Compounds / metabolism
  • Stereoisomerism

Substances

  • Alkaloids
  • Piperidines
  • Spiro Compounds
  • spiro(4-azaindan-1,2'-piperidine)
  • spiro(6-azaindan-1,2'-piperidine)
  • Palladium
  • Nicotine
  • Anabasine