Biology-oriented synthesis of benzopyrano[3,4-c]pyrrolidines

Bioorg Med Chem. 2015 Jun 15;23(12):2895-903. doi: 10.1016/j.bmc.2015.02.044. Epub 2015 Mar 4.

Abstract

A natural product inspired synthesis of 6,6,5-tricyclic compounds via a silver(I)-catalyzed formal 1,3-dipolar cycloaddition of coumarins with α-iminoesters was developed. The reaction proceeds in a stepwise reaction course under formation of the trans-substituted diastereomer with respect to the 1,3-dipole and shows a broad substrate scope.

Keywords: Azomethine ylide; Biology-oriented synthesis (BIOS); Catalysis; Coumarin; [2+3] cycloaddition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemical synthesis
  • Azo Compounds / chemistry
  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry
  • Coumarins / chemical synthesis
  • Coumarins / chemistry*
  • Cycloaddition Reaction
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Silver / chemistry*
  • Thiosemicarbazones / chemical synthesis
  • Thiosemicarbazones / chemistry

Substances

  • Azo Compounds
  • Benzopyrans
  • Coumarins
  • Pyrrolidines
  • Thiosemicarbazones
  • azomethine
  • Silver
  • coumarin