Formal synthesis of (±)-cycloclavine

J Org Chem. 2014 Jan 3;79(1):122-7. doi: 10.1021/jo4023588. Epub 2013 Nov 27.

Abstract

An efficient formal synthesis of (±)-cycloclavine is achieved in seven steps and 27% overall yield from the known 2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehyde. Key features include an iron(III)-catalyzed aza-Cope-Mannich cyclization and an intramolecular Heck reaction or a self-terminating 6-exo-trig aryl radical-alkene cyclization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaldehyde / analogs & derivatives*
  • Acetaldehyde / chemistry
  • Catalysis
  • Cyclization
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Indoles / chemistry*
  • Iron / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • 2-(4-bromo-1-tosyl-1H-indol-3-yl)acetaldehy
  • Indole Alkaloids
  • Indoles
  • cycloclavine
  • Iron
  • Acetaldehyde