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KAKEN_18H01984seika.pdf
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多環性構造を有する生物活性天然物の効率的合成法の開発
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タカンセイ コウゾウ オ ユウスル セイブツ カッセイ テンネンブツ ノ コウリツテキ ゴウセイホウ ノ カイハツ
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Takansei kōzō o yūsuru seibutsu kassei tennenbutsu no kōritsuteki gōseihō no kaihatsu
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Development of the efficient synthetic methods of multi-cyclic biologically active natural products
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千田, 憲孝
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チダ, ノリタカ
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Chida, Noritaka
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慶應義塾大学・理工学部 (矢上) ・教授
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Research team head
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科研費研究者番号 : 50197612
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2021
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科学研究費補助金研究成果報告書
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2020
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本研究においては、複雑な多環性構造を有する天然物を効率的に合成する手法の確立を目的とし,1)ヨウ化サマリウムを用いるアリルベンゾエート/アルデヒドの環化反応とRubbotom酸化による新規橋頭位二重結合導入反応を鍵工程とするタキソールの第二世代合成、2)不斉転写を伴う連続的シグマトロピー転位反応と,ヨウ化サマリウムによるCD環の一段階構築、アミド選択的な求核反応を利用する五環性アルカロイド、ネオツベロステモニンの全合成研究を行い,両化合物の全合成を達成した。新規多環性分子合成の立体選択的キラル合成に有用な新規反応の確立と多環性生物活性天然物の合成法の開発に成功した。
In this project, to establish the synthetic way to structurally complex natural products possessing multi-cyclic system, total syntheses of taxol and neotuberostemonine were investigated. On the synthetic study of taxol, total synthesis was achieved utilizing the Sm-mediated construction of eight-membered ring and the introduction of bridge-head olefin by the double Rubottom oxidation as the key transformation. On the other hand, the total synthesis of neotuberostemonine was also accomplished. The sequential sigmatropic rearrangements, Sm-mediated cyclization and lactam-selective nucleophilic addition were employed for the synthesis. These achievements established the stereoselective chiral synthesis of structurally complex multi-cyclic natural products.
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研究種目 : 基盤研究 (B) (一般)
研究期間 : 2018~2020
課題番号 : 18H01984
研究分野 : 有機合成化学
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