Synthesis of Tamiflu by Using a Barium-Catalyzed Asymmetric Diels-Alder-Type Reaction
In pursuit of a better route: A new catalytic asymmetric synthesis of Tamiflu was developed. The key transformation was an asymmetric Diels–Alder‐type reaction of 1 and 2 catalyzed by a barium/F2‐FujiCAPO complex in the presence of a CsF co‐catalyst to construct the core of Tamiflu (see scheme; TMS=...
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| Veröffentlicht in: | Angewandte Chemie (International ed.) 2009-01, Vol.48 (6), p.1070-1076 |
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| container_end_page | 1076 |
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| container_issue | 6 |
| container_start_page | 1070 |
| container_title | Angewandte Chemie (International ed.) |
| container_volume | 48 |
| creator | Yamatsugu, Kenzo Yin, Liang Kamijo, Shin Kimura, Yasuaki Kanai, Motomu Shibasaki, Masakatsu |
| description | In pursuit of a better route: A new catalytic asymmetric synthesis of Tamiflu was developed. The key transformation was an asymmetric Diels–Alder‐type reaction of 1 and 2 catalyzed by a barium/F2‐FujiCAPO complex in the presence of a CsF co‐catalyst to construct the core of Tamiflu (see scheme; TMS=trimethylsilyl). The product was converted into Tamiflu in 11 steps on a gram scale. |
| doi_str_mv | 10.1002/anie.200804777 |
| format | Article |
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The key transformation was an asymmetric Diels–Alder‐type reaction of 1 and 2 catalyzed by a barium/F2‐FujiCAPO complex in the presence of a CsF co‐catalyst to construct the core of Tamiflu (see scheme; TMS=trimethylsilyl). The product was converted into Tamiflu in 11 steps on a gram scale.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200804777</identifier><identifier>PMID: 19016287</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH Verlag</publisher><subject>Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; barium ; Barium - chemistry ; Catalysis ; Cyclization ; cycloaddition ; dienes ; homogeneous catalysis ; Models, Chemical ; Oseltamivir - chemical synthesis ; Oseltamivir - chemistry ; Stereoisomerism ; tamiflu</subject><ispartof>Angewandte Chemie (International ed.), 2009-01, Vol.48 (6), p.1070-1076</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. 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| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie (International ed.), 2009-01, Vol.48 (6), p.1070-1076 |
| issn | 1433-7851 1521-3773 |
| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Antiviral Agents - chemical synthesis Antiviral Agents - chemistry barium Barium - chemistry Catalysis Cyclization cycloaddition dienes homogeneous catalysis Models, Chemical Oseltamivir - chemical synthesis Oseltamivir - chemistry Stereoisomerism tamiflu |
| title | Synthesis of Tamiflu by Using a Barium-Catalyzed Asymmetric Diels-Alder-Type Reaction |
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