Asymmetric total synthesis of (+)-virosine A via sequential nucleophilic cyclizations onto an activated formamide

J Org Chem. 2012 Apr 6;77(7):3215-21. doi: 10.1021/jo202651t. Epub 2012 Mar 12.

Abstract

The first synthesis of tetracyclic alkaloid virosine A is reported. The natural alkaloid was prepared in only 13 steps, in an enantioenriched form. The azabicyclo[2.2.2]octane core was efficiently assembled using a key Vilsmeier-Haack and Mannich cyclizations sequence performed in one pot.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry*
  • Cyclization
  • Euphorbiaceae / chemistry*
  • Formamides / chemistry*
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkaloids
  • Formamides
  • Heterocyclic Compounds, 4 or More Rings
  • virosine A
  • formamide