Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
1, 6-Dihydro-3 (2H)-pyridinones. V. Total Synthesis of (±)-Eburnamonine
今西 武宮下 賢一中井 章井上 誠花岡 美代次
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キーワード: isomerization of imine
ジャーナル フリー

1983 年 31 巻 4 号 p. 1191-1198

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抄録
3-Ethyl-3-methoxycarbonylmethylpiperidine (20) was prepared via the unsaturated aldehyde (12) derivel from benzyl 1, 6-dihydro-3 (2H)-pyridinone-1-carboxylate (5b). N-Chlorination of 20 and subsequent exposure to a base afforded rel-(2S, 3R)-3-ethyl-2-hydroxypiperidine-3-acetic acid γ-lactone (3) in a good yield. According to the known method, the lactone (3) was converted into (±)-eburnamonine (1) and (±)-epieburnamonine (31). A possible pathway from 20 to 3 is also discussed.
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© The Pharmaceutical Society of Japan
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