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Keywords:

  • alkylation;
  • puraquinonic acid;
  • quaternary stereocenter;
  • quinones;
  • total synthesis
Thumbnail image of graphical abstract

Distant relative: The configuration of the quaternary stereocenter in puraquinonic acid (see scheme, right) is defined by groups far removed from the point of asymmetry. The use of a bicyclic thioglycolate lactam to set the quaternary stereocenter at an early stage cuts the length of the synthesis of the natural product by nearly two thirds.