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Keywords:

  • biomimetic synthesis;
  • cycloaddition;
  • cyclization;
  • natural products;
  • neurological agents
Thumbnail image of graphical abstract

Efficient and adaptable: The key steps in the total synthesis of ent-nanolobatolide, the enantiomer of the novel and potent neuroprotective agent, involve an oxidative ring expansion of (−)-menthone, a Nazarov cyclization, an intermolecular Diels–Alder reaction, and an intramolecular epoxide-opening reaction (see scheme). The two latter transformations provided evidence in support of the speculated biosynthetic pathway.