YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
降圧作用を有するProtoberberine誘導体の合成研究(第4報)11-O-Demethylxylopinine(11-hydroxy-5,6,13,13a-tetrahydro-2,3,10-trimethoxy-8H-dibenzo[a, g]quinolizine)およびアシル誘導体の合成ならびに(±)-Xylopinineの光学分割(複素環式化合物の合成研究(第531報)
亀谷 哲治丹生 淳郷池田 茂夫富永 倶弘岩城 利一郎
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1973 年 93 巻 9 号 p. 1120-1126

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When O-demethylxylopinine (XIII) was synthesized from 1-(3-hydroxy-4-methoxybenzyl)-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline (XI), 11-hydroxy-9-hydroxymethyl-2, 3, 10-trimethoxy-5, 6, 13, 13a-tetrahydro-8H-dibenzo [a, g] quinolizine (XIV) was also formed. Accordingly, in order to prevent formation of this by-product, 11-benzyloxy-2, 3, 10-trimethoxy-5, 6, 13, 13a-tetrahydro-8H-dibenzo [a, g] quinolizine (XII), which was synthesized by the Eschweiler-Clarke reaction of 1-(3-benzyloxy-4-methoxybenzyl)-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline (X), was debenzylated to give XIII in a good yield. On the other hand, several 11-acyloxyprotoberberine derivatives. (XVIIa-f), which were expected as hypotensives, were synthesized by acylation of XIII with acetic anhydride and acid chloride. Optical resolution of (±)-xylopinine was carried out from which optically active xylopinine was obtained.

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