Abstract
The first total synthesis of Monocillin I related macrolides has been achieved by a convergent and stereospecific route involving the palladium - catalyzed coupling of a functionnalized chiral vinylstannane with the appropriate dimethoxy bromomethyl isocoumarin. Cleavage conditions of the isocoumarin ring were then found for the preparation of a precursor hydroxy acid. The 14-membered macrolide was obtained in the Mitsunobu reaction conditions, and the required natural conjugated dienone epoxide system of Monocillin I was generated stereospecifically from that macrocyclic precursor.
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