A concise synthesis of physostigmine from skatole and activated aziridine via alkylative cyclization

Org Lett. 2000 Apr 6;2(7):953-5. doi: 10.1021/ol005603u.

Abstract

A concise synthetic route to physostigmine has been developed, where the key step relies on the alkylative cyclization of 1,3-dimethylindole with (Z)-aziridine catalyzed by Sc(OTf)3 and TMSCI in dichloromethane at -30 degrees C, to give 8 in 90% yield, which, in turn, can be readily converted into physostigmine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Aziridines / chemistry*
  • Cholinesterase Inhibitors / chemical synthesis*
  • Cyclization
  • Indicators and Reagents
  • Physostigmine / chemical synthesis*
  • Skatole / chemistry*
  • Solvents

Substances

  • Aziridines
  • Cholinesterase Inhibitors
  • Indicators and Reagents
  • Solvents
  • Physostigmine
  • Skatole