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Lactams. XXIV. Alkaline hydrolysis of 1-benzyl-2-piperidone derivatives: application to cis-trans isomerization of the 5-ethyl-2-oxo-4-piperidineacetic acid system
- フォーマット:
- 論文
- 責任表示:
- Fujii, Tozo ; Ohba, Masashi ; Akiyama, Shigeaki
- 言語:
- 英語
- 出版情報:
- 日本薬学会, 1985-04-25
- 著者名:
- 掲載情報:
- Chemical & pharmaceutical bulletin
- ISSN:
- 0009-2363
- 巻:
- 33
- 通号:
- 4
- 開始ページ:
- 1716
- 終了ページ:
- 1720
- バージョン:
- publisher
- 概要:
- In boiling 2.5 N solution of KOH in 40% (w/w) aqueous EtOH, the lactams (±)-5a, b, d were hydrolyzed to an extent of 75-98% within 8-20 h, attaining equilibrium with the corresponding ω-amino acid derivatives (±)-6a, b, d. The potassium salt (±)-8,generated in situ from the translactam acid (±)-7,was equilibrated with the ring-opened product (±)-6f and the recyclized cis isomer (±)-5f in a ratio of 57 : 15 … : 28 within ca. 45 h under similar reaction conditions. The cis-N-(2-arylethyl) analog (-)-9 was converted into the trans-lactam acid (+)-13,a key synthetic precursor for the 8-hydroxy-9,10-dimethoxybenzo [a] quinolizidine-type Alangium alkaloids, through application of such alkaline hydrolytic cis-trans equilibration followed by debenzylation. 続きを見る
- URL:
- http://hdl.handle.net/2297/7627