Synthesis of (±)-Serralongamine A and the Revised Structure of Huperzine N

J Org Chem. 2016 Mar 18;81(6):2629-34. doi: 10.1021/acs.joc.6b00025. Epub 2016 Mar 4.

Abstract

A revised structure for the Lycopodium alkaloid huperzine N is proposed and confirmed by synthesis. The key synthetic steps involve an epimerization of a cis-5-oxodecahydroquinoline to the corresponding trans isomer and a coupling, followed by a diastereoselective hydrogenation using Wilkinson's catalyst to incorporate the pyridylmethyl moiety. This route allowed the alkaloid serralongamine A to be synthesized for the first time, and two additional steps led to the revised structure of huperzine N, both products bearing an unusual decahydroquinoline stereostructure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrogenation
  • Lycopodium / chemistry*
  • Molecular Structure
  • Quinolines / chemistry
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry*
  • Stereoisomerism

Substances

  • Quinolines
  • Sesquiterpenes
  • cis-5-oxodecahydroquinoline
  • huperzine N
  • serralongamine A