Coreximine関連化合物の合成研究(第1報) : Eschweiler-Clarke反応条件下におけるO-Demethylcoreximineの合成 : 複素環式化合物の合成研究第162報

概要

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7-Benzyloxy-1-(3,4-bisbenzyloxybenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (XIV) was submitted to the Eschweiler-Clarke reaction in 98% formic acid and 37% formaldehyde solution, and 7-benzyloxy-1-(3,4-bisbenzyloxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (XV) was obtained in 5.9% yield, with trans-2,10,11-trisbenzyloxy-3-methoxy-5,6,13,13a-tetrahydro-8H-dibenzo-[a, g] quinolizine (XVI) in 80.4% yield. XVI was also obtained in 83.1% yield by refluxing XIV in a mixture of acetic acid and 37% formaldehyde solution, and dehydrogenation of XVI with mercuric acetate gave a quarternary ammonium salt (XIX). Debenzylation of XVI in ethanolic hydrochloric acid gave (±)-O-demethylcoreximine (XVII) whose methylation with diazomethane gave (±)-norcoralydine (XVIII), which was identified with an authentic sample through admixture, infrared spectra, and by thinlayer chromatography.
公益社団法人日本薬学会の論文
1967-02-25