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oseltamivir phosphate (tamiflu), swainsonine and platensimycin

dc.contributor.advisorSaičić, Radomir
dc.contributor.otherFerjančić, Zorana
dc.contributor.otherBihelović, Filip
dc.contributor.otherMatović, Radomir
dc.creatorTrajković, Miloš D.
dc.date.accessioned2016-07-16T13:12:39Z
dc.date.available2016-07-16T13:12:39Z
dc.date.available2020-07-03T10:16:08Z
dc.date.issued2015-12-25
dc.identifier.urihttp://nardus.mpn.gov.rs/handle/123456789/5892
dc.identifier.urihttp://eteze.bg.ac.rs/application/showtheses?thesesId=3181
dc.identifier.urihttps://fedorabg.bg.ac.rs/fedora/get/o:11541/bdef:Content/download
dc.identifier.urihttp://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=47673103
dc.description.abstractRazvijene su dve enantioselektivne formalne sinteze oseltamivir-fosfata i totalna enantioselektivna sinteza svainsonina. U prvoj sintezi oseltamivir-fosfata kao ključne reakcije korišćene su enantioselektivna aldolna adicija hiralnog borovog enolata na hiralni aldehid, čime su formirana dva nova stereocentra i aldolna kondenzacija kojom je nagrađen cikloheksenski prsten. U drugoj sintezi oseltamivir-fosfata kao ključne reakcije korišćene su alilovanje hiralnog aldehida u vodenim uslovima i ciklizaciona metateza za formiranje cikloheksenskog skeleta. Na osnovu rezultata do kojih se došlo u sintezi oseltamivira, razvijena je enantioselektivna sinteza Garner-ovog aldehida, koja se zasniva na transfer-hidrogenolizi odgovarajućeg tioestra. Totalna enantioselektivna sinteza svainsonina počiva na taktičkoj kombinaciji organokatalizovane aldolne adicije i reduktivnog aminovanja, čime se formira pirolidinski skelet sa tri definisana stereocentra, dok je piperidinski prsten zatvoren primenom još jedne reakcije reduktivnog aminovanja. U okviru sintetičke studije platenzimicina ostvaren je prodor prema formalnoj sintezi oksatetracikličnog Nicolaou-ovog intermedijera, gde je uspešno napravljen spiro-biciklični intermedijer. Kao ključne reakcije za sintezu ovog jedinjenja iskorišćene su Mukaiyama–Michael-ova reakcija, praćena 6–endo-trig ciklizacijom, dekarboksilativno alilovanje i ciklizaciona metateza.sr
dc.description.abstractTwo enantioselective formal syntheses of oseltamivir phosphate and the enantioselective total synthesis of swainsonine have been accomplished. The key reactions in the first synthesis of oseltamivir phosphate were enantioselective aldol additions of boron enolate to chiral aldehyde, that formed two new stereocenters, and aldol condensation for the construction of cyclohexene ring. In the second synthesis of oseltamivir phosphate, the pivotal steps were allylation of chiral aldehydes under aqueous conditions and ring closing metathesis for the formation of cyclohexene ring. Based on the results for the first synthesis of oseltamivir, a new enantioselective synthesis of Garner aldehyde was developed, that hinges on the transfer hydrogenation of the corresponding thioester. Total enantioselective synthesis of swinsonine was based on the tactical combination of organocatalyzed aldol addition and reductive amination for the formation of the pyrrolidine skeleton with three contiguous stereocenter, followed by the piperidine ring formation by a second reductive amination. Within a synthetic study on platensimycin, a breakthrough towards formal synthesis of oxatetracyclic Nicolaou's intermediate was achieved, by successfully synthesizing the spirobicyclic intermediate. The key steps in the synthesis of this compound were Mukaiyama-Michael's reaction followed by 6-endo-trig cyclisation, decarboxylative allylation and ring closing metathesis.en
dc.formatapplication/pdf
dc.languagesr
dc.publisherУниверзитет у Београду, Хемијски факултетsr
dc.rightsopenAccessen
dc.sourceУниверзитет у Београдуsr
dc.subjectoseltamivir-fosfatsr
dc.subjectoseltamivir phosphateen
dc.subjectTamifluen
dc.subjectswainsonineen
dc.subjectplatensimycinen
dc.subjecttotal syntesisen
dc.subjectenantioselective syntesisen
dc.subjectTamiflusr
dc.subjectsvainsoninsr
dc.subjectplatenzimicinsr
dc.subjecttotalna sintezasr
dc.subjectenantioselektivna sintezasr
dc.titleEnantioselektivne sinteze jedinjenja značajnih za medicinu: oseltamivir-fosfat (tamifly), svainsonin i platenzimicinsr
dc.titleoseltamivir phosphate (tamiflu), swainsonine and platensimycinen
dc.typedoctoralThesisen
dc.rights.licenseBY-NC-ND
dcterms.abstractСаичић, Радомир; Ферјанчић, Зорана; Бихеловић, Филип; Матовић, Радомир; Трајковић, Милош Д.;
dc.identifier.fulltexthttp://nardus.mpn.gov.rs/bitstream/id/30310/Disertacija3742.pdf
dc.identifier.fulltexthttp://nardus.mpn.gov.rs/bitstream/id/30311/Trajkovic_Milos_D.pdf


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