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タイトル: Lactams. XXVI. Regioselectivity in the mercuric acetate- edetic acid oxidation of the ethyl 1-(2-aryl-2-hydroxyethyl)-3- ethyl-4-piperidineacetate system: Enhancement by a benzyloxy group in the aryl moiety and by the 3,4-cis configuration
著者: Fujii, Tozo
Ohba, Masashi link image
Tsuchida, Michiko
Saito, Kiyoe
Hirano, Yuko
Sakaguchi, Jun
藤井, 澄三
大場, 正志
土田, 美智子
斎藤, 紀代江
平野, 裕子
坂口, 順
発行日: 1986年
出版社(者): 日本薬学会
雑誌名: Chemical & pharmaceutical bulletin
ISSN: 0009-2363
巻: 34
号: 2
開始ページ: 496
終了ページ: 507
キーワード: 1, 3-disubstituted piperidine
mercuric acetate-EDTA oxidation
piperidone regioselective formation
pyridine base quaternization
sodium borohydride phenacyl group reduction
benzylic alcohol catalytic hydrogenolysis
piperidoine trans-cis isomerization
piperidone isomer spectroscopic differentiation
抄録: A quantitative analytical study to determine the isomer ratios of the 6-piperidones (type 7) and 2-piperidones (type 5) produced by the mercuric acetate-edetic acid (EDTA) oxidation of 1-(2-aryl-2-hydroxyethyl)-3-alkylpiperidines (±)-4c, d, f, h, 4e, g, i, j, and (±)-38 was carried out. It has been found that all the substrates with a benzyloxy group in the aryl moiety, regardless of its location, undergo oxidation at the 6-position preferentially as compared with the debenzyloxy derivatives such as (±)-4a, b. Comparison of the quantitative data from 4e and (±)-4f with those from (±)-4b indicated that the cis acetate chain at the 4-position increases the extent of the 6-oxidation, whereas a trans acetate chain at the same position has little effect. These two factors enhance the practical value of the "cincholoipon-incorporating method" for chiral syntheses of the 1-type Alangium alkaloids, in which the mercuric acetate-EDTA oxidation of 4e, g, i, j to the 6-piperidones (type 3)is one of the key synthetic operations.
URI: http://hdl.handle.net/2297/7621
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/2297/7621



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