Synthesis of bicyclic proline derivatives by the aza-Cope-Mannich reaction: formal synthesis of (±)-acetylaranotin

Chemistry. 2015 Mar 2;21(10):4141-7. doi: 10.1002/chem.201405811. Epub 2015 Jan 28.

Abstract

Herein we suggest an approach to oxygenated bicyclic amino acids based on an aza-Cope-Mannich rearrangement. Seven distinct amino acid scaffolds analogous to the natural products were prepared on a gram scale with precise control of stereochemistry. Successful implementation of our strategy resulted in the formal synthesis of acetylaranotin.

Keywords: amino acids; medicinal chemistry; natural products; rearrangement; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Catalysis
  • Molecular Structure
  • Oxepins / chemical synthesis*
  • Oxepins / chemistry
  • Proline / chemistry*

Substances

  • Amino Acids
  • Aza Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • Oxepins
  • acetylaranotin
  • Proline