|Budget Amount *help
¥1,300,000 (Direct Cost : ¥1,300,000)
Fiscal Year 2000 : ¥600,000 (Direct Cost : ¥600,000)
Fiscal Year 1999 : ¥700,000 (Direct Cost : ¥700,000)
In recent years a series of structurally related and biologically active polycyclic aromatic alkaloids possessing pyrido [2,3,4-kl] acridine or pyrrolo [2,3,4-kl] acridine skeleton have been isolated from marine organisms. We achieved synthesis of the alkaloids including iminoquinoline-quinone structure, e.g. 11-hydroxyascididemin and kuanoniamine A.In this research project we have studied total synthesis of meridine and cystodamine, and synthesis of pyrrolo [2,3,4-kl]- acridine (1) and benzo [b] pyrrolo [4,3,2-de][1,10] phenanthrolin-8 (11H)-one (2), a common skeleton of plakinidine A-C.
(a) Meridine and cystodamine were synthesized by using hetero Diels-Alder reaction between 4-methoxy-(or 4-chloro-) 5,8-quinolinedione and 2-nitrocinnamaldehyde dimethylhydrazone as a key step.
(b) 7-methylbenzo [b][1,10] phenanthrolin-4 (1H)-one (3) was obtained from o-aminoacetophenone and o-bromonitrobenzene. However we found that synthesis of 2 from 3 will be difficult.
(c) Pyrrolo [2,3,4-kl] acridin-1 (2H)-one possessing the same skeleton as 1 was synthesized from o-Aminoacetophenone and m-bromonitrobenzene via 2-acetylpyrrolo [2,3,4-kl] acridin-1 (2H)-one (4). 6,11-dihydrobenzo [b] pyrrolo [4,3,2-de][1,10] phenanthroline-5, 8-dione possessing the same skeleton as 2 was synthesized from 4.