ベンゾ［c］フェナンスリジン·アルカロイドおよび関連化合物の合成研究

Abstract

Benzo[c]phenanthridine alkaloids are distributed in Papaveraceous and Rutaceous plants and classified into two categories of fully aromatized bases and partially hydrogenated bases(B/C-cis-11-hydroxyhexahydrobenzo[c]phenanthridine skeleton). They have long history, in which the first isolation of chelidonine, a partially hydrogenated base, from Papaveraceous plant, was reported in 1839. Over a century later nitidine and fagaronine, O4-type fully aromatized bases isolated from Rutaeceous plant, attracted much attention because of their antitumor activity. At present, a variety of pharmacological effects are recognized in natural and unnatural species. We, about forty years ago, started synthetic studies on fully aromatized bases focusing on structure-activity relationship of antitumor activity and succeeded in establishing widely-applicable synthetic methods. Recently the enantioselective synthesis of chelidonine was completed. Thus, in this review, we present our chemical history for the synthesis of benzo[c]phenanthridine bases.