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 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.
Appukkuttan
Prasad
P
Department of Chemistry, University of Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.
Dehaen
Wim
W
Van der Eycken
Erik
E
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis*; D001392:Azocines / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D005702:Galantamine / Q000737:chemistry*; D008670:Metals / Q000737:chemistry; D008872:Microwaves; D008956:Models, Chemical
D047151:Amaryllidaceae Alkaloids; D001392:Azocines; D001688:Biological Products; D008670:Metals; D005702:Galantamine; C048309:apogalanthamine