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タイトル: | Catalytic asymmetric formal synthesis of beraprost |
著者: | Kobayashi, Yusuke Kuramoto, Ryuta Takemoto, Yoshiji https://orcid.org/0000-0003-1375-3821 (unconfirmed) |
著者名の別形: | 竹本, 佳司 |
キーワード: | Bifunctional catalysis Hydrogen bonding Organocatalyst Oxa-Michael Prostacyclin |
発行日: | 18-Dec-2015 |
出版者: | Beilstein-Institut |
誌名: | Beilstein Journal of Organic Chemistry |
巻: | 11 |
開始ページ: | 2654 |
終了ページ: | 2660 |
抄録: | The first catalytic asymmetric synthesis of the key intermediate for beraprost has been achieved through an enantioselective intramolecular oxa-Michael reaction of an α, β-unsaturated amide mediated by a newly developed benzothiadiazine catalyst. The Weinreb amide moiety and bromo substituent of the Michael adduct were utilized for the C-C bond formations to construct the scaffold. All four contiguous stereocenters of the tricyclic core were controlled via Rh-catalyzed stereoselective C-H insertion and the subsequent reduction from the convex face. |
著作権等: | © 2015 Kobayashi et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
URI: | http://hdl.handle.net/2433/219534 |
DOI(出版社版): | 10.3762/bjoc.11.285 |
PubMed ID: | 26734111 |
出現コレクション: | 学術雑誌掲載論文等 |
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