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Total Synthesis of the Marine Antibiotic Pestalone and its Surprisingly Facile Conversion into Pestalalactone and Pestalachloride A


  • This work was supported by Evangelisches Studienwerk e.V. Villigst (PhD stipend to N. S.). We gratefully acknowledge generous gifts of chemicals from Chemetall GmbH and Sanofi-Aventis Deutschland GmbH. We also thank Prof. Dr. A. Griesbeck for support concerning the photochemical experiments.


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Surprise, surprise! The total synthesis of the marine natural product pestalone (1), a highly substituted benzophenone with strong antibiotic acitivity, has provided insight into the surprising tendency of this and related molecules to undergo intramolecular Cannizzaro–Tishchenko-type reactions. Pestalone can be readily converted into pestalachloride A, a strongly antifungal metabolite isolated from an endophytic fungus, by simple treatment with ammonia at pH 8.

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