7,8-Disubstituted 1-Benzylisoquinoline関連化合物の合成研究その3 dl-Cularicineの合成

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Bischler-Napieralski reaction of the phenolic bromo-amide (VII), which was prepared by the condensation of 4-benzyloxy-2-bromo-5-hydroxyphenethylamine (V) with methyl 2-bromo-4,5-methylenedioxyphenylacetate (VI) and reduction with NaBH_4 of the resultant benzyldihydroisoquinoline (VIII) gave 7-benzyloxy-5-bromo-1-(2-bromo-4,5-methylenedioxybenzyl)-8-hydroxy-1,2,3,4-tetrahydroisoquinoline (IX). N-Methylation of IX gave X. The Ullmann reaction of X in the presence of potassium carbonate and cupric oxide in pyridine gave 6-benzyloxy-4-bromo-1-methyl-9,10-methylenedioxy-1,2,3,12,12a-pentahydrobenzoxepino [2,3,4-i, j] isoquinoline (XI). Subsequent debromination of XI with LiAlH_4 gave XII and debenzylation of XII with hydrogen over 10% palladiumcharcol gave dl-cularicine (I). I was identified with natural cularicine by infrared and nuclear magnetic resonance spectral comparisons.
公益社団法人日本薬学会の論文
1972-10-25