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Keywords:

  • antifungal agents;
  • natural products;
  • rearrangements;
  • sulfur heterocycles

The quest for superior antifungal agents will be aided by the unprecedented sulfur migration of an epidithioketopiperazine (EDKP) in a highly stereoselective manner and in high yield. The rearrangement provides a short route to compounds in the same family as aspirochlorine (1), a potent inhibitor of fungal protein synthesis. In this family one of the dithio sulfur atoms is anchored to a dihydrobenzofuran ring that is spiro fused to the piperazine ring.

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