TAKAYAMA Hiroyuki, Ph.D. / Associate Professor
Division of Organic and Medicinal Chemistry
Department of Pharmaceutical Sciences
1. Development of new catalytic reactions promoted by a transition metal complex.
2. The efficient total synthesis of bioactive natural products.
3(2H)-Furanones and oxazoles are a common structure in a range of important pharmaceuticals. Diarylketones are also frequently found in natural products and pharmaceuticals, and they are good precursors for non-steroidal antiestrogen drugs and diarylmethyl compounds. Transition metal-catalyzed reaction of unsaturated systems has recently proven to be a powerful method for the construction of a variety of carbo- and heterocycles. The vinyl- and arylpalladium intermediates are formed by oxidative addition of a carbon-halogen bond to palladium(0). we have presented a cyclization-carbonylation-cyclization coupling reaction of propargylic compounds catalyzed by palladium(II) complexes. Symmetrical ketones possessing two heterocyclic groups were obtained in moderate to excellent yields. We are investigating other new tandem reactions based on the cyclization-carbonylation-cyclization strategy.
1. Takayama H, Kato K, Akita H, Synthesis of (4R,5S)-melithiazols F and I. European Journal of Organic Chemistry, 3, 644-649 (2006).
2. Yasuhara S, Sasa M, Kusakabe T, Takayama H, Kimura M, Mochida T, Kato K, Cyclization-CarbonylationCyclization Coupling Reactions of Propargyl Acetates and Amides with Palladium(II)-Bisoxazoline Catalysts. Angewandte Chemie,International Edition, 50, 3912-3915 (2011).
3. Yen W P, Tsai S E, Uramaru N, Takayama H, Wong F F., One-flask synthesis of pyrazolo[3,4-d]pyrimidines from 5-aminopyrazoles and mechanistic study. Molecules, 22, 820 (2017).