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Keywords:

  • Natural products;
  • Biomimetic synthesis;
  • Nucleophilic addition;
  • Nitrogen heterocycles;
  • Lithiation

Abstract

A versatile route for the conversion of ferulic acid into biologically relevant molecules is presented. The compatibility of a number of protection and activation strategies with the 1,2-addition of a variety of O-, N-, S-, and C-nucleophiles to ferulic acid is evaluated. In particular, this report contains the first systematic study of the addition of (hetero)aryllithium reagents to 3-phenylpropenoyl Weinreb amides. The relevance of this “bioinspired” method is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, curcuminoids, and (heteroaryl) chalcones.