Total Synthesis of Lycopalhine A

Org Lett. 2016 Mar 18;18(6):1494-6. doi: 10.1021/acs.orglett.6b00338. Epub 2016 Mar 7.

Abstract

The total synthesis of lycopalhine A has been accomplished. The synthesis features construction of the tricyclic system via cleavage of a cyclopropane ring and an ensuing intramolecular Michael addition, stereoselective introduction of a 2-aminoethyl moiety via a reaction of allyltrimethylsilane to a sulfonyliminium ion, and a stereoselective intramolecular aldol reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Cyclopropanes / chemistry
  • Lycopodium / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Sulfones / chemistry

Substances

  • Alkaloids
  • Cyclopropanes
  • Sulfones
  • lycopalhine A
  • cyclopropane