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Microwave-assisted Suzuki-Miyaura and Stille cross-coupling reactions for the synthesis of highly electron-rich 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.

[reaction: see text] A novel, microwave-enhanced six-step synthesis was devised for the synthesis of N-shifted buflavine analogues. Microwave-enhanced Suzuki-Miyaura cross-coupling and ring-closing metathesis reactions were used as the key steps. Microwave irradiation was found to enhance the ring-closing metathesis reaction to generate the otherwise difficultly obtainable medium-sized ring system of the target molecules.