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Keywords:

  • cyclizations;
  • eliminations;
  • natural products;
  • ring-closing reactions;
  • total synthesis
Thumbnail image of graphical abstract

A highly efficient enantioselective total synthesis of the natural antibiotic IKD-8344 is achieved through a convergent route. This route features an otherwise impossible concurrent formation of the THF rings from a linear polyketide precursor through intramolecular O alkylations of mesylates in competition with normally rather facile β elimination and/or α racemization reactions (see scheme, Ms=methanesulfonyl).