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31 生体触媒を活用した汎用性キラル素子の創製と天然物合成への応用(口頭発表の部)
http://hdl.handle.net/10110/00018235
http://hdl.handle.net/10110/0001823569ddf4df-d344-400a-842a-60cf6d06f3b8
名前 / ファイル | ライセンス | アクション |
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SympoChemNaturalProducts_36_234to241_Toyooka (443.7 kB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2018-03-01 | |||||
タイトル | ||||||
タイトル | 31 生体触媒を活用した汎用性キラル素子の創製と天然物合成への応用(口頭発表の部) | |||||
タイトル | ||||||
言語 | en | |||||
タイトル | 31 SYNTHESIS OF VERSATILE CHIRAL BUILDING BLOCKS BY ADOPTING BIOCATALYSIS AND THEIR APPLICATION TO NATURAL PRODUCT SYNTHESIS | |||||
言語 | ||||||
言語 | jpn | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
豊岡, 尚樹
× 豊岡, 尚樹× 神, 誠× 西野, 彰× 田中, 敬子× 吉田, 泰子× 百瀬, 雄章 |
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著者別名 | ||||||
姓名 | Toyooka, Naoki | |||||
著者別名 | ||||||
姓名 | Jin, Makoto | |||||
著者別名 | ||||||
姓名 | Nishino, Akira | |||||
著者別名 | ||||||
姓名 | Tanaka, Keiko | |||||
著者別名 | ||||||
姓名 | Yoshida, Yasuko | |||||
著者別名 | ||||||
姓名 | Momose, Takefumi | |||||
その他(別言語等)のタイトル | ||||||
その他のタイトル | 31 SYNTHESIS OF VERSATILE CHIRAL BUILDING BLOCKS BY ADOPTING BIOCATALYSIS AND THEIR APPLICATION TO NATURAL PRODUCT SYNTHESIS | |||||
抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | Biocatalysis is recognized as a useful tool for organic synthesis, especially for the asymmetric synthesis of natural products. As part of our efforts to synthesize versatile chiral building blocks by adopting biocatalysis, we developed the lipase-catalyzed desymmetrization of the meso-glycol 1 and the meso-diacetate 2 to afford both enantiomers of the ketol acetate 4 as an optically pure state, respectively. The desymmetrization of the meso-glycol 5 was also achieved to give the monoacetate (-)-6, which was led in three steps to the decalin (+)-19. Enantiomerization of (+)-19 was readily accomplished to give (-)-19. On the other hand, baker's yeast reduction of the β-keto ester 7 proceeded in a highly enantioselective manner and furnished the homochiral piperidone (-)-8 in good yield. The enantiomer (+)-8 was obtained by the lipase-mediated optical resolution of (±)-8. Thus, we achieved highly efficient synthesis of both enantiomers of chiral building blocks 4, 6, 8. The versatility of 4, 6 and 8 for natural product synthesis was demonstrated by the first total synthesis of(-)-cassine (11), (+)-spectaline (12), (-)-indolizidine 235B' and the formal synthesis of (-)-dihydropinidine, (-)-indolizidine 207A, 209B, (-)-polygodial, (-)-warburganal, (-)-drimenin, and prosopinie, respectively. | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | 天然有機化合物討論会講演要旨集 36, 234-241.(1994) | |||||
書誌情報 |
天然有機化合物討論会講演要旨集 en : Symposium on the Chemistry of Natural Products, symposium papers 巻 36, p. 234-241, 発行日 1994-09-20 |
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書誌レコードID | ||||||
収録物識別子タイプ | NCID | |||||
収録物識別子 | AN00154136 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.24496/tennenyuki.36.0_234 | |||||
フォーマット | ||||||
内容記述タイプ | Other | |||||
内容記述 | application/pdf | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
論文ID(NAID) | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | NAID | |||||
関連識別子 | 110006679296 | |||||
出版者 | ||||||
出版者 | 天然有機化合物討論会 | |||||
資源タイプ(DSpace) | ||||||
内容記述タイプ | Other | |||||
内容記述 | Article |