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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
出現コレクション:2.査読済論文(薬)

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