This review involves the recent progress of "The Chemistry of Benzo [c] phenanthridine Alkaloids" developed in our laboratory. Structural establishment of naturally occurring four new amides, arnottianamide, isoarnottianamide, integriamide, and iwamide, was performed by deriving from chelerythrine, nitidine, avicine, and decarine, respectively, by using the Baeyer-Villiger type oxidation of an immonium group, developed in our group. The fully aromatized O
5-benzo [c] phenanthridine alkaloids, chelirubine, chelilutine, sanguilutine, and sanguirubine, were synthesized by photo-cyclization of an enamide or by the revised Robinson method. In general, this revised method is also applicable to the synthesis of the 8, 9-oxygenated O
4-bases, for example nitidine was prepared by this method in 40% total yield. The induced shift of
1H-NMR signals of oxybases is discussed.
抄録全体を表示