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Keywords:

  • allyl silanes;
  • annulation;
  • naphthoquinone methides;
  • polycycles;
  • synthetic methods
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Pharmaceutically useful dihydronaphthopyran derivatives were obtained in good yield by the regio- and stereoselective annulation of ortho-naphthoquinone methides with allyl silanes. The ortho-naphthoquinone methides were generated in situ from 1-siloxymethyl-1,4-epoxy-1,4-dihydronaphthalenes under FeCl3 catalysis (see scheme; allyl-TMS=allyltrimethylsilane, TBS=tert-butyldimethylsilyl, TMS=trimethylsilyl).