(±)-O-Demethylstepharotineおよび(±)-O-Methylstepharotineの合成 : 複素環式化合物の合成研究第312報

概要

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Treatment of 7-benzyloxy-1-(3-benzyloxy-4,5-dimethoxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (III) with acetic acid and 37% formaldehyde solution resulted in the progress of the Mannich reaction and protoberberine bases (VI and VII) were obtained. These bases were identified with the authentic sample obtained by the treatment of the hydrochloride of III with 37% formaldehyde solution. Debenzylation of VI and VII gave the phenolic bases, X ((±)-O-demethylstepharotine) and XI, and their methylation with diazomethane gave the same (±)-O-methylstepharotine (XII). XI was also obtained by debenzylation of III to IX and its Mannich reaction. The Eschweiler-Clarke reaction of III gave VI and VII accompanied by a small amount of 7-benzyloxy-1-(3-benzyloxy-4,5-dimethoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (VIII) which was identified with an authentic specimen.
公益社団法人日本薬学会の論文
1969-05-25