Abstract: Utilization of the palladium-catalyzed reactions of vinyl triflates 8 obtained from model N-substituted (1 1aS)-2, 3, 5, 10, 11, 1 la-hexahydro-2, 5, 1 l-trioxo-1H-pyrrolo [2, 1- c][1, 4] benzodiazepines (5, 6) either with 0-(tributylstanny1) acrylates or acrylic esters and amides yields coupled products (9-13) having the basic anthramycin framework. Generation of the enol triflates from the 2-keto precursors is regiospecific, introducing the double bond ...