ChemInform Abstract: Intramolecular Base-Free Sonogashira Reaction for the Synthesis of Benzannulated Chiral Macrocycles Embedded in Carbohydrate Templates

A variety of furanoses and pyranoses (14 examples) bearing a bromobenzyl and a terminal alkynyl group undergo the reaction in the presence of a heterogeneous basic alumina-supported palladium catalyst and CuI as co-catalyst to give benzannulated 10- to 13-membered macrocycles containing the carbohydrate moiety.