18 Protoberberineアルカロイドの新規合成とBenzo[c]phenanthridineアルカロイド(±)-Ambinineの全合成(口頭発表の部)

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We have accomplished a novel and efficient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-alkylated alkaloids. And (±)-ambinine, a B/C-hexahydro benzo[c]phenanthridine alkaloid possessing a unique substitution pattern on the aromatic rings was totally synthesized from the corresponding 13-alkylberbine. Condensation of the bromophenethylamine (7) with the benzaldehyde (8), followed by reduction afforded the secondary amine (9), which was converted into the N-phenethylisoquinolone (10) on treatment with α-chloro-α-methylthioacetyl chloride (2). The isoquinolone (10) was conveniently transformed into 2,3,9,10-tetraoxygenated protoberberine alkaloids, (±)-canadine, (±)-tetrahydropalmatine, (±)-stylopine, and (±)-sinactine. On the other hand, 10 gave the 4-alkylated isoquinolone (13) which was converted into the 13-alkylprotoberberine alkaloids, (±)-thalictricavine, (±)-corydaline, (±)-tetrahydrocorysamine, and (±)-13-ethyltetrahydropalmatine. Convenient transformation of 13-methylberbine (21), prepared according to the above method, into (±)-ambinine (24) was successfully achieved by our biomimetic method.
天然有機化合物討論会の論文
1991-09-07