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PH-PR-OHBA-M-1946.pdf1.36 MBAdobe PDF
タイトル: Quinolizidines. XIII. Syntheses of (±)-and (-)-Alangimarckines
著者: Fujii, Tozo
Kogen, Hiroshi
Yoshifuji, Shigeyuki
Ohba, Masashi link image
藤井, 澄三
古源, 寛
吉藤, 茂行
大場, 正志
発行日: 1985年 5月25日
出版社(者): 日本薬学会
雑誌名: Chemical & pharmaceutical bulletin
ISSN: 0009-2363
巻: 33
号: 5
開始ページ: 1946
終了ページ: 1954
キーワード: Alangium alkaloid alangimarckine
diethyl phosphorocyanidate amide formation
Bischler-Napieralski cyclization
sodium borohydride reduction
catalytic hydrogenolysis
TLC epimer differentiation
NMR epimer differentiation
CD epimer differentiation
抄録: The first total synthesis of the Alangium alkaloid alangimarckine (8) has been accomplished in the form of a racemic modification by means of an initial coupling of the (±)-tricyclic amino acid 6 with tryptamine and succeeding steps proceeding through the intermediates (±)-7,(±)-10,and (±)-9. The 1'-epimers (±)-12 and (±)-11 were also produced in this reaction sequence. A parallel sequence of conversions starting with the (-)-tricyclic amino acid 6 yielded the chiral molecule (-)-8 via the intermediates (+)-7,(+)-10,and (+)-9,together with the 1'-epimer (-)-11 via (-)-12. The identity of the synthetic (-)-8 with natural alangimarckine unequivocally established the structure and absolute configuration of this alkaoid. The assignments of the configuration at C-1'of 8,9,11,and 12 were based on five criteria, namely, the ratio of products from the NaBH_4 reduction of (±)-10,thin-layer chromatographic mobility, and proton and carbon-13 nuclear magnetic resonance and circular dichroism spectroscopic features.
URI: http://hdl.handle.net/2297/7609
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/2297/7609



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