Convergent Stereospecific Total Synthesis of Monochiral Monocillin I Related Macrolides

Article abstract of DOI:10.1016/S0040-4039(00)77712-4

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 functionalized 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 reqired natural conjugated dienone epoxide system of Monocillin I was generated stereospecifically from that macrocyclic precursor.