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| ファイル | 記述 | サイズ | フォーマット | |
|---|---|---|---|---|
| jacs.9b02220.pdf | 2.77 MB | Adobe PDF | 見る/開く |
| タイトル: | Total Synthesis of Caprazamycin A: Practical and Scalable Synthesis of syn-β-Hydroxyamino Acids and Introduction of a Fatty Acid Side Chain to 1,4-Diazepanone |
| 著者: | Nakamura, Hugh Tsukano, Chihiro    https://orcid.org/0000-0002-9361-0857 (unconfirmed)Yoshida, Takuma Yasui, Motohiro Yokouchi, Shinsuke Kobayashi, Yusuke Igarashi, Masayuki Takemoto, Yoshiji https://orcid.org/0000-0003-1375-3821 (unconfirmed) |
| 著者名の別形: | 塚野, 千尋 小林, 祐輔 竹本, 佳司 |
| 発行日: | 29-May-2019 |
| 出版者: | American Chemical Society (ACS) |
| 誌名: | Journal of the American Chemical Society |
| 巻: | 141 |
| 号: | 21 |
| 開始ページ: | 8527 |
| 終了ページ: | 8540 |
| 抄録: | The first total synthesis of caprazamycin A (1), a representative liponucleoside antibiotic, is described. Diastereoselective aldol reactions of aldehydes 12 and 25–27, derived from uridine, with diethyl isocyanomalonate 13 and phenylcarbamate 21 were investigated using thiourea catalysts 14 or bases to synthesize syn-β-hydroxyamino acid derivatives. The 1, 4-diazepanone core of 1 was constructed using a Mitsunobu reaction, and the fatty acid side chain was introduced using a stepwise sequence based on model studies. Notably, global deprotection was realized using palladium black and formic acid without hydrogenating the olefin in the uridine unit. |
| 著作権等: | This is the accepted manuscript of the article, which has been published in final form at https://doi.org/10.1021/jacs.9b02220. The full-text file will be made open to the public on 8 May 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 |
| URI: | http://hdl.handle.net/2433/243177 |
| DOI(出版社版): | 10.1021/jacs.9b02220 |
| PubMed ID: | 31067040 |
| 出現コレクション: | 学術雑誌掲載論文等 |
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