Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine

Org Lett. 2012 Feb 3;14(3):934-7. doi: 10.1021/ol203463n. Epub 2012 Jan 13.

Abstract

The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Azides / chemistry*
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Cyclization
  • Models, Molecular
  • Molecular Structure
  • Polycyclic Compounds / chemical synthesis*
  • Quinolines / chemical synthesis*

Substances

  • Azides
  • Bridged Bicyclo Compounds, Heterocyclic
  • Polycyclic Compounds
  • Quinolines
  • meloscine