Total synthesis of (+)-hygrine via asymmetric phase-transfer catalytic alkylation

J Org Chem. 2006 Aug 18;71(17):6690-2. doi: 10.1021/jo061108l.

Abstract

The first enantioselective synthesis of (+)-hygrine (1) is reported. 1 was obtained in 12 steps with 29% overall yield and 97% ee via asymmetric phase-transfer catalytic alkylation and ring-closing metathesis as key steps. The absolute configuration of (+)-hygrine could be directly confirmed as R.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Catalysis
  • Molecular Structure
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Stereoisomerism

Substances

  • Pyrrolidines
  • hygrine