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- 松村 功啓
- 京都大学工学部合成化学教室
書誌事項
- タイトル別名
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- New methods for the synthesis of piperidine alkaloids and their precursors using anodic oxidation as a key reaction.
- デンキョク サンカ オ カギハンノウ ト スル ピペリジン アルカロイド オヨ
この論文をさがす
説明
This article describes new methods to introduce a variety of substituents into the α, β or γ position of a piperidine ring by utilizing anodic oxidation as a key reaction. The following patterns of anodic oxidation were exploited to activate the α and, β positions of N-methoxycarbonylpiperidines A; (1) anodic oxidation of A in methanol containing Et4NOTs to give the α-methoxylated products B, (2) anodic oxidation of A in acetic acid to give the a, /9-bisacetoxylated products C, (3) anodic oxidation of A to afford β-halogenated α-hydroxy-or α-methoxy-piperidine derivatives D, and (4) anodic decarboxylation of pipecolinic acid derivatives to afford B or C. The γ- position of A was activated by converting B or D into β, γ-unsaturated a-methoxypiperidine derivatives E. The activated compounds B, C, D and E were used as useful precursors to introduce substituents into the desired positions of piperidine ring, and some alkaloids containing a piperidine skeleton such as coniine, optically active N-methylconiine, conhydrine, and eburnamonine were synthesized from these precursors.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 48 (9), 814-823, 1990
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390001205277340032
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- NII論文ID
- 130000926357
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 3680236
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDLサーチ
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