アミノ酸類似および糖類似ニトロンを用いる多種類の生理活性物質合成

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Author: 田村, 修ほか

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Publication date: 2006-07-10

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Note (General)：: 金沢大学自然科学研究科1)糖などのヘミアセタールから多酸素官能基化された環状ニトロンの一般合成法を開発した.この反応の応用例として,L-xyloseより得られるニトロンを用いてアザ糖類であるcodonopsinine, hyacinthacine A_1,及びhyacinthacine A_2の合成...

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Material Type: 文書・図像類
Title: アミノ酸類似および糖類似ニトロンを用いる多種類の生理活性物質合成
Author/Editor: 田村, 修
Tamura, Osamu
Author Heading: 田村, 修
Tamura, Osamu
Publication Date: 2006-07-10
Publication Date (W3CDTF): 2006-07-10
Alternative Title: Synthetk Studies on Multi Sorts of Biologically Active Cormpounds Using Nitrones Related to Amino Acids and Sugars
Periodical title: 平成16(2004)年度科学研究費補助金基盤研究(C) 研究成果報告書概要 = 2004 Fiscal Year Final Research Report Summary
No. or year of volume/issue: 2003 – 2004
Volume: 2003 – 2004
Pages: 2p.-
Text Language Code: jpn
Subject Heading: ニトロン
アミノ酸
糖類
環化付加反応
求核付加反応
生理活性物質
合成
nitrone
amino acids
sugars
cycloaddition
nucleophilic addition
biologically active compounds
synthesis
Target Audience: 一般
Note (General): 金沢大学自然科学研究科
1)糖などのヘミアセタールから多酸素官能基化された環状ニトロンの一般合成法を開発した.この反応の応用例として,L-xyloseより得られるニトロンを用いてアザ糖類であるcodonopsinine, hyacinthacine A_1,及びhyacinthacine A_2の合成を行った.2)光学活性な環状ニトロンのアリルアルコール類との環化付加反応やα-置換アクリル酸誘導体との環化付加反応を用いて,4-ヒドロキシ-4-置換グルタミン酸類の立体選択的な一般合成法を開発した.この反応の応用例として天然甘味物質monatinやlycoperdic acidの新規合成法を明らかにした.3)窒素上に糖由来の不斉補助基を有するニトロンの分子内環化付加反応を用いてイソロイシン由来の側鎖を有するピロールアルカロイドfunebrineおよびfunebralの光学活性体の最初の全合成を行った.4)ニトロンの分子間反応における重複不斉誘導を用いて,人におけるnicotineの代謝産物である(3'R,5'S)-3'-hydroxycotinineの合成を行った.5)Diels-Alder反応やニトロンの環化付加反応に代表されるペリ環状反応の複素環合成への応用例を総説にまとめた.
(1)A method for the synthesis cyclic nitrones having multi-oxygen functionalities from herniacetals such as sugars was explored. Thus, the nitrones were prepared by TBAT-mediated desilylative cyclization of ω-mesyloxy-O-tert-butyldiphenylsilyloximes, readily prepared from sugar derivatives by a consecutive treatment with O-tert-butyldiphenylsilylhydroxylamine and with mesyl chloride. As an application of this method, concise synthes of codonopsine, hyacinthacine A_1, and hyacinthacine A_2 were reality accomplished from the cyclic nitrone, which was obtained from protected L-xylose.(2)A cyclic nitrone derived from (S)-phenylglycinol reacted with allyl alcohols in the presence of MgBr_2OEt_2 to give cycloadducts stereoselectively. The reaction was applied to syntheses of monatin (a natural sweetener) and lycoperdic acid. In contrast to cycloaddition with allyl alcohols, reactions of the cyclic nitrone with a-substituted acrylates in the absence of MgBr_2・OEt_2 gave cycloadducts having opposite C4-stcreochemistries. The reaction was used for the synthesis of 4-epi-monatin.(3)The first syntheses of (-)-funebrine and (-)-funebral were achieved. The syntheses feature sequential formation of the nitrone from methyl glyoxylate with a gulose-derived oxime, transesterification with (E)-crotyl alcohol, and intramolecular cycloaddition. The major cycloadduct was readily elaborated to amino lactone, the key synthetic intermediate of (-)-funebrine and (-)-funebral.(4)To synthesize (3'R,5'S)-3'-hydroxycotinine, the main metabolite of nicotine, cycloaddition of C-(3-pyridyl)nitrones with (2R)-and (2S)-N-(acryloyl)bornane-10,2-sultam {(2R)-and (2S)-sultam] was examined. Among them, L-gulose-derived nitrone underwent stereoselective cycloaddition with (2S)-sultam to afford the cycloadduct, which was elaborated to (3'R,5'S)-3'-hydroxyeotinine.(5)Applications of Diets-Alder reactions and cycloaddition of nitrones, representative peri-cyclic reactions to synthesis of heterocyclic compounds were reviewed.
研究課題/領域番号:15590003, 研究期間(年度):2003 – 2004
出典：「アミノ酸類似および糖類似ニトロンを用いる多種類の生理活性物質合成」研究成果報告書　課題番号15590003（KAKEN：科学研究費助成事業データベース（国立情報学研究所））（https://kaken.nii.ac.jp/ja/report/KAKENHI-PROJECT-15590003/155900032004kenkyu_seika_hokoku_gaiyo/)を加工して作成
DOI: 10.24517/00063166
Source: https://kanazawa-u.repo.nii.ac.jp/?action=repository_action_common_download&item_id=56892&item_no=1&attribute_id=26&file_no=1
https://kanazawa-u.repo.nii.ac.jp/?action=repository_action_common_download&item_id=56892&item_no=1&attribute_id=26&file_no=1
Access Restrictions: 限定公開
Rights (production): CC BY-NC-ND
Related Material: https://nrid.nii.ac.jp/ja/search/?kw=30257141
https://kaken.nii.ac.jp/ja/grant/KAKENHI-PROJECT-15590003/
https://kaken.nii.ac.jp/ja/report/KAKENHI-PROJECT-15590003/155900032004kenkyu_seika_hokoku_gaiyo/
Data Provider (Database): 国立情報学研究所 : 学術機関リポジトリデータベース（IRDB）（機関リポジトリ）
https://irdb.nii.ac.jp
Original Data Provider (Database): 金沢大学 : 金沢大学学術情報リポジトリKURA