Total synthesis of (-)-cassine

Org Lett. 2003 Jan 9;5(1):27-9. doi: 10.1021/ol0201916.

Abstract

The PdCl(2)-catalyzed cyclization of amino allylic alcohol 16 gave the cyclized product 17a with excellent diastereoselectivity. The versatility of compound 17a as the building block for synthesizing cis-2,6-disubstituted piperidine alkaloids has been demonstrated by a total synthesis of (-)-cassine (1). [reaction--see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Cassia / chemistry*
  • Ketones / chemical synthesis*
  • Molecular Structure
  • Piperidines / chemical synthesis*

Substances

  • Alkaloids
  • Ketones
  • Piperidines
  • cassine