Traceless solid-phase synthesis of mappicine ketone library via multiple chemoselective palladium-catalyzed reactions on benzenesulfonate linker

We report here a solid-phase synthesis of a library of mappicine ketone, a leading antiviral compound with activity against herpes viruses and human cytomegalovirus. The synthesis is based on multiple chemoselective palladium-catalyzed reactions involving a regioselective intramolecular Heck reaction at C-2, substitution of Cl at C-7 by Suzuki-Miyaura cross-coupling reaction and Buchwald-Hartwig amination, and reductive cleavage of the benzenesulfonate linker at C-1O.