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Formal Synthesis of (-)-Oseltamivir Phosphate
dc.creator | Trajković, Milos | |
dc.creator | Ferjančić, Zorana | |
dc.creator | Saičić, Radomir | |
dc.date.accessioned | 2018-11-22T00:25:25Z | |
dc.date.available | 2018-11-22T00:25:25Z | |
dc.date.issued | 2013 | |
dc.identifier.issn | 0039-7881 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/1596 | |
dc.description.abstract | The formal synthesis of (-)-oseltamivir phosphate (Tamiflu (TM)) was accomplished starting from (S)-pyroglutamic acid. The synthesis comprised two carbon-carbon bond forming reactions, the first one being a diastereoselective, indium-mediated allylation of a pyroglutamic aldehyde derivative. However, attempts to effect the second carbon-carbon bond formation - cyclohexene ring closure - using an enol-exo aldolization of a dialdehyde resulted in the formation of a product with the opposite regioselectivity. This shortcoming could be overcome by using a reaction sequence of Mannich methylenation/ring-closing metathesis, which provided the desired regioisomer in high yield. | en |
dc.publisher | Georg Thieme Verlag Kg, Stuttgart | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172027/RS// | |
dc.rights | restrictedAccess | |
dc.source | Synthesis, Stuttgart | |
dc.subject | antiviral agents | en |
dc.subject | allylation | en |
dc.subject | cyclization | en |
dc.subject | metathesis | en |
dc.subject | total synthesis | en |
dc.title | Formal Synthesis of (-)-Oseltamivir Phosphate | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Саичић, Радомир; Трајковиц, Милос; Ферјанчић, Зорана; | |
dc.citation.volume | 45 | |
dc.citation.issue | 3 | |
dc.citation.spage | 389 | |
dc.citation.epage | 395 | |
dc.identifier.wos | 000314632500018 | |
dc.identifier.doi | 10.1055/s-0032-1317948 | |
dc.citation.other | 45(3): 389-395 | |
dc.citation.rank | M22 | |
dc.description.other | Supplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3495] | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-84872923889 |