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タイトル: Quinolizidines. X. Stereospecific Syntheses of (±)-9-Demethylpsychotrine and (±)-10-Demethylpsychotrine
著者: Fujii, Tozo
Ohba, Masashi link image
藤井, 澄三
大場, 正志
発行日: 1985年 1月25日
出版社(者): 日本薬学会
雑誌名: Chemical & pharmaceutical bulletin
ISSN: 0009-2363
巻: 33
号: 1
開始ページ: 144
終了ページ: 151
キーワード: Alangium alkaloid desmethylpsychotrine
stereospecific synthesis
lactim ether alkylation
sodium borohydride reduction
catalytic hydrogenolysis
benzyl ether cleavage
diethyl phosphorocyanidate amide formation
Bischler-Napieralski cyclization
^<13>C-NMR dihydroisoquinoline structure determination
抄録: With the aim of establishing the structure of the Alangium alkaloid desmethylpsychotrine, stereospecific syntheses of two alternative structures, (±)-9-demethylpsychotrine (1) and (±)-10-demethylpsychotrine (2), have been achieved through a"lactim ether route."The synthesis of (±)-1 started with an initial condensation of the lactim ether 6,derived from the translactam ester 5,with 3-benzyloxy-4-methoxyphenacyl bromide (7a) and proceeded through the intermediates 8a, 9a, 10c, 10a, 11a, 12a, 13a, 14a, and 15a. A parallel sequence of conversions starting with 6 and 4-benzyloxy-3-methoxyphenacyl bromide (7b) produced (±)-2. The ^<13>C nuclear magnetic resonance spectra of (±)-1 and (±)-2 confirmed their endocyclic double bond structure in the dihydroisoquinoline moiety. Spectral comparison of (±)-1 and (±)-2 with natural desmethylpsychotrine suggested formula 1 to be the most likely structure of this alkaloid.
URI: http://hdl.handle.net/2297/7611
資料種別: Journal Article
版表示: publisher

このアイテムを引用あるいはリンクする場合は次の識別子を使用してください。 http://hdl.handle.net/2297/7611



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