8-Bromo-1,2,3,4-tetrahydro-1-〔p-(5-hydroxymethyl-2-methoxy-phenoxy)benzyl〕-6,7-methylenedioxyisoquinolineの合成 : 複素環式化合物の合成研究第225報

概要

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In order to synthesize cepharanthine (I), some examinations were made on two methods ; the Ullmann condensation of two benzylisoquinoline-type bases and preliminary formation of one diphenyl ether structure and then bringing that closer to I. For the first method, IV was obtained either by debenzylation of II, or by the Clemmensen reduction of V and VI, and the Ullmann condensation of IV and III was attempted but the reaction did not materialize. Then the reaction of the diphenyl ether compound (XV) and XIII with the amine (XIV) was carried out respectively by the fusion reaction and the Schotten-Baumann reaction to obtain the amide (XVI) which was derived to the O-acetyl compound (XVIII), and the Bischler-Napieralski reaction of XVIII, followed by reduction with sodium borohydride gave the tetrahydroisoquinoline compound (XX), whose structure was identified through elemental analysis, and infrared and NMR spectra.
公益社団法人日本薬学会の論文
1968-04-25