Synthetic Organic Chemistry
Hiroto NAGAOKA, Ph.D., Professor
Kazuhiko Takatori, Ph.D., Associate Professor
Atushi KISHIDA, B.Sc., Research Associate
The major research efforts in our laboratory are the total synthesis of biologically active natural products bearing unique molecular architectures and the development of new synthetic methodologies. The present synthesis targets include paclitaxel, illudines, coriolin and tocotrienol (antitumor compounds), zaragozic acid (inhibitor of squalene synthetase), merrilactone A (neuromodulatory compound), phomactins (inhibitors of PAF), and gibberellins and anthridiogen-An (plant hormones). For the construction of the polycyclic carbon skeleton, we have also investigated efficient synthetic methodologies and novel synthetic reagents. Methodologies recently developed include one-step synthesis of bicyclic oxacyclopentanecarboxylates from bis-α,β-unsaturated esters by samarium(II) iodide-induced reductive coupling-Dieckmann condensation, synthesis of cyclopentanones from 1,2-cyclotutanedicarboxylates by a new type of samarium(II)-induced ring-expansion reaction and novel preparation method for optically active trisubstituted cyclopentanones by a samarium(II) iodide-induced cascade reaction.