Cepharanthine関連化合物の合成研究(第2報) : 1-(3-Bromo-4-methoxybenzyl)-1,2,3,4-tetrahydro-6-methoxy-2-methyl-7-isoquinolinolの合成複素環式化合物の合成研究第183報

概要

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As the starting material for the synthesis of cepharanthine, 1-(3-bromo-4-methoxybenzyl)-1,2,3,4-tetrahydro-6-methoxy-2-methyl-7-isoquinolinol (IIa) was successfully prepared a different route. Anisaldehyde (VI) was derived to the ester (IX) through azlactone VII and VIII, and IX was condensed with 4-benzyloxy-3-methoxyphenethylamine (V)to form the amide (XI), which was cyclized by the usual Bischler-Napieralski reaction to form the 3,4-dihydroisoquinoline compound (XII). Reduction of the methiodide (XIII) of XII with sodium borohydride afforded II which was found to be also obtainable by the reduction of the hydrochloride of XII with sodium borohydride, and its product submitted to the Eschweiler- Clarke reaction with formic acid and formaldehyde. Treatment of II with 2O% ethanolic hydrochloric acid afforded the debenzylated compound (IIa) as a hexane adduct. The attempted Ullmann reaction of IIa and III to obtain IV did not materialize.
公益社団法人日本薬学会の論文
1967-07-25