40 アルカロイド合成における電解酸化法の応用 : (±)-Oxomaritidine,(±)-Oxocrinine,(±)-Flavinantine,(±)-Pallidine,(±)-Amurine,(±)-Cryptopleurine等の全合成

抄録

Recent progress of electro-oxidation method in organic chemistry has been provided a new possibility for the synthesis of complex organic compounds. We were investigated an application of this method for the synthesis of complicated natural alkaloids and able to synthesize the titled compounds in excellent yield via anodic oxidation. Syntheses of crinine type alkaloids (±)-Oxocrinine, (±)-oxomaritidine, and related crinine type Amaryllidaceae alkaloids were synthesized from norbelladines 3 via cross conjugated dienone 4 by anodic oxidation. Syntheses of morphinandienone alkaloids (±)-Flavinanthine, (±)-pallidine, and (±)-amurine 10 were synthesized by electro-oxidation of 1-benzylisoquinolines 9 in high yield followed by hydrolysis. Syntheses of phenanthroquinolizidine alkaloids (±)-Cryptopleurine 19 was synthesized through electro-oxidation of substituted hexahydroquinolizinone 14.