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Keywords:

  • antitumor agents;
  • cycloaddition;
  • natural products;
  • photochemistry;
  • total synthesis
Thumbnail image of graphical abstract

The total synthesis of the natural product (−)-silvestrol (1) has been accomplished and features enantioselective [3+2] photocycloaddition of a substituted 3-hydroxyflavone and methyl cinnamate promoted by a chiral Brønsted acid. Initial biological studies indicate a 5–10-fold greater activity of silvestrol as an inhibitor of protein synthesis in HeLa cells than its 1′′′′ diastereomer.