SYNTHESIS OF (-)-GLOEOSPORONE

Abstract The homochiral lactone ( 5 ) and the oxazolidinone ( 9 ), together with the phosphoniumsalt ( 15 ), serve as key building blocks for the enantioselective synthesis of the ( Z )-bis(silyloxy) ester ( 17 ), whose photochemical conversion into the ( E )-isomer ( 18 ) constitutes a formal synthesis of the antifungal macrocyclic lactone (−)-gloeosporone ( 2 ). The building blocks ( 5 ), ( 9 ), ( 15 ), and ( 17 ) are used to construct the enantiomerically pure ester ( 18 ) thus constituting a formal synthesis of (−)-gloeosporone ( 2 ).