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Keywords:

  • antitumor agents;
  • biological activity;
  • dioxinones;
  • Prins cyclization;
  • total synthesis
Thumbnail image of graphical abstract

Three become one: The title compound can be prepared in 26 steps by employing a unified Prins cyclization strategy to construct both tetrahydropyran rings (see scheme). The route combines two similar dioxinone fragments and one aldehyde component to generate the core structure. (−)-Exiguolide selectively inhibits the growth of A549 cancer cells at low concentrations; the triene side chain and the Z-enoate geometry are both necessary for this cytotoxicity.