Suzuki-Miyaura and Stille Reactions as Key Steps in the Synthesis of Diversely Functionalized Amaryllidaceae Alkaloid Analogs Bearing a 5,6,7,8-Tetrahydrobenzo[c,e]Azocine Skeleton

Microwave-assisted Suzuki-Miyaura and Stille cross-coupling reactions for the synthesis of highly electronrich and diversely functionalized biaryl intermediates are presented. Microwave-irradiation has been demonstrated to be a very powerful tool for performing difficult transition metal-catalyzed cross-coupling reactions with unfavorably substituted coupling partners. The key biaryl intermediates were used for the microwave-enhanced construction of the 5,6,7,8- tetrahydrobenzo[c,e]azocine skeleton of the Apogalanthamine analogs. The success of the strategy is demonstrated by synthesizing a number of hitherto unknown, diversely functionalized, natural product analogs.