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[{"key": "dc.contributor.advisor", "value": "Pihko, Petri", "language": null, "element": "contributor", "qualifier": "advisor", "schema": "dc"}, {"key": "dc.contributor.advisor", "value": "Siitonen, Juha", "language": null, "element": "contributor", "qualifier": "advisor", "schema": "dc"}, {"key": "dc.contributor.author", "value": "Cederstr\u00f6m, Mona", "language": null, "element": "contributor", "qualifier": "author", "schema": "dc"}, {"key": "dc.date.accessioned", "value": "2018-04-30T05:39:48Z", "language": null, "element": "date", "qualifier": "accessioned", "schema": "dc"}, {"key": "dc.date.available", "value": "2018-04-30T05:39:48Z", "language": null, "element": "date", "qualifier": "available", "schema": "dc"}, {"key": "dc.date.issued", "value": "2017", "language": null, "element": "date", "qualifier": "issued", "schema": "dc"}, {"key": "dc.identifier.other", "value": "oai:jykdok.linneanet.fi:1869637", "language": null, "element": "identifier", "qualifier": "other", "schema": "dc"}, {"key": "dc.identifier.uri", "value": "https://jyx.jyu.fi/handle/123456789/57796", "language": null, "element": "identifier", "qualifier": "uri", "schema": "dc"}, {"key": "dc.description.abstract", "value": "Tutkielman kirjallisessa osiossa k\u00e4sitell\u00e4\u00e4n steroidirungon eri synteesimenetelmi\u00e4.\nSynteesimenetelm\u00e4t esitell\u00e4\u00e4n niiden synteesistrategioiden mukaan, jotka on edelleen\njaoteltu niiss\u00e4 esiintyvien reaktioiden tai yleisten l\u00e4ht\u00f6aineiden pohjalta. Johdannossa\nk\u00e4yd\u00e4\u00e4n lyhyesti l\u00e4pi steroidien rakenne ja niiden biosynteesi ihmisen elimist\u00f6ss\u00e4.\nT\u00e4m\u00e4n j\u00e4lkeen aloitetaan synteesien tarkastelu sekosteroidi v\u00e4livaiheisiin pohjautuvista\neli steroidirungon keskiosan rakentamiseen keskittyvist\u00e4 synteesistrategioista, joista\nsiirryt\u00e4\u00e4n steroidirungon renkaat j\u00e4rjestyksess\u00e4 rakentaviin synteeseihin. N\u00e4iden\nsynteesien j\u00e4lkeen palataan luonnonmukaisempaan steroidien synteesitapaan eli\npolysyklisaatioon. Lopuksi esitell\u00e4\u00e4n lyhyesti, kuinka homosteroidirunko voidaan\nmuuttaa steroidirungoksi.\n\nTutkielman kokeellisessa osiossa toistettiin Takanon ja Ogasawaran1 3-metoksi-15,16-\ndehydroestronin stereoselektiivinen synteesi. Synteesin ensimm\u00e4iset vaiheet, Danen\ndieenin 175 valmistaminen Knochelin ja Soorukramin menetelm\u00e4ll\u00e42 onnistui hyvin (yli\n95 % saanto). Raseemista ketonia 280 saatiin valmistettua Mihelich-Eckhoffhapetuksella3\nsuhteellisen hyvin (68 %). Synteesin avainvaiheessa Diels-Alder-reaktiossa\nilmeni ongelmia, sill\u00e4 reaktiosta ei saatu Takanon ja Ogasawaran julkaisun1 mukaista\nreaktiotuotetta, vaan sen isomeeria iso-283 (56 %). Kun haluttua isomeeria (283)\nonnistuttiin saamaan (46 %), havaittiin, ett\u00e4 tuotteen stereokemia ei vastannut aiemmin\njulkaistun tuotteen stereokemiaa. Synteesi\u00e4 jatkettiin alkyloinnilla (55 %) ja\npelkistyksell\u00e4 (57 %), joista j\u00e4lkimm\u00e4inen korjasi reaktiotuotteen stereokemian halutuksi\nja samalla Takanon ja Ogasawaran julkaisun1 mukaiseksi. Reitin saantoa yritettiin\nparantaa vaihtamalla alkyloinnin ja pelkistyksen j\u00e4rjestyst\u00e4, mik\u00e4 ei kuitenkaan auttanut\nasiaa. Pelkistyksen saanto vaihtoehtoista reitti\u00e4 pitkin j\u00e4i heikommaksi (38 %) ja\nalkyloinnin p\u00e4\u00e4tuotteeksi muodostui O-alkylointituote 291 (49 %). Synteesin viimeinen\nvaihe, retro-Diels-Alder-reaktio ei sujunut odotusten mukaisesti, vaan tuotti\nhuomattavasti kirjallisuutta1 heikommat saannot (20\u201340 %). Lopputuotteeksi saatiin (\u2013\n)-3-metoksi-15,16-dehydroestronia (278), jonka kokonaissaanto oli vain n. 5 %.", "language": "fi", "element": "description", "qualifier": "abstract", "schema": "dc"}, {"key": "dc.description.provenance", "value": "Submitted using Plone Publishing form by Mona Cederstr\u00f6m (mojacede) on 2018-04-30 05:39:46.760054. Form: Pro gradu -lomake (https://kirjasto.jyu.fi/julkaisut/julkaisulomakkeet/pro-gradu-lomake). JyX data: [jyx_publishing-allowed (fi) =True]", "language": "en", "element": "description", "qualifier": "provenance", "schema": "dc"}, {"key": "dc.description.provenance", "value": "Submitted by jyx lomake-julkaisija (jyx-julkaisija.group@korppi.jyu.fi) on 2018-04-30T05:39:48Z\nNo. of bitstreams: 2\nURN:NBN:fi:jyu-201804302396.pdf: 9476285 bytes, checksum: 0344d5e8ab77e2c97ce2554951f78dd1 (MD5)\nlicense.html: 4860 bytes, checksum: 5728b397a921c77dbc28aafb5148af47 (MD5)", "language": "en", "element": "description", "qualifier": "provenance", "schema": "dc"}, {"key": "dc.description.provenance", "value": "Made available in DSpace on 2018-04-30T05:39:48Z (GMT). No. of bitstreams: 2\nURN:NBN:fi:jyu-201804302396.pdf: 9476285 bytes, checksum: 0344d5e8ab77e2c97ce2554951f78dd1 (MD5)\nlicense.html: 4860 bytes, checksum: 5728b397a921c77dbc28aafb5148af47 (MD5)\n Previous issue date: 2018", "language": "en", "element": "description", "qualifier": "provenance", "schema": "dc"}, {"key": "dc.format.extent", "value": "1 verkkoaineisto (146 sivua)", "language": null, "element": "format", "qualifier": "extent", "schema": "dc"}, {"key": "dc.format.mimetype", "value": "application/pdf", "language": null, "element": "format", "qualifier": "mimetype", "schema": "dc"}, {"key": "dc.language.iso", "value": "fin", "language": null, "element": "language", "qualifier": "iso", "schema": "dc"}, {"key": "dc.rights", "value": "In Copyright", "language": "en", "element": "rights", "qualifier": null, "schema": "dc"}, {"key": "dc.subject.other", "value": "synteesimenetelm\u00e4t", "language": null, "element": "subject", "qualifier": "other", "schema": "dc"}, {"key": "dc.subject.other", "value": "3-metoksi-15", "language": null, "element": "subject", "qualifier": "other", "schema": "dc"}, {"key": "dc.subject.other", "value": "16-dehydroestroni", "language": null, "element": "subject", "qualifier": "other", "schema": "dc"}, {"key": "dc.title", "value": "Steroidirungon synteesimenetelm\u00e4t ja 3-metoksi-15,16-dehydroestronin stereoselektiivinen synteesi", "language": null, "element": "title", "qualifier": null, "schema": "dc"}, {"key": "dc.type", "value": "master thesis", "language": null, "element": "type", "qualifier": null, "schema": "dc"}, {"key": "dc.identifier.urn", "value": "URN:NBN:fi:jyu-201804302396", "language": null, "element": "identifier", "qualifier": "urn", "schema": "dc"}, {"key": "dc.type.ontasot", "value": "Pro gradu -tutkielma", "language": "fi", "element": "type", "qualifier": "ontasot", "schema": "dc"}, {"key": "dc.type.ontasot", "value": "Master\u2019s thesis", "language": "en", "element": "type", "qualifier": "ontasot", "schema": "dc"}, {"key": "dc.contributor.faculty", "value": "Matemaattis-luonnontieteellinen tiedekunta", "language": "fi", "element": "contributor", "qualifier": "faculty", "schema": "dc"}, {"key": "dc.contributor.faculty", "value": "Faculty of Sciences", "language": "en", "element": "contributor", "qualifier": "faculty", "schema": "dc"}, {"key": "dc.contributor.department", "value": "Kemian laitos", "language": "fi", "element": "contributor", "qualifier": "department", "schema": "dc"}, {"key": "dc.contributor.department", "value": "Department of Chemistry", "language": "en", "element": "contributor", "qualifier": "department", "schema": "dc"}, {"key": "dc.contributor.organization", "value": "University of Jyv\u00e4skyl\u00e4", "language": "en", "element": "contributor", "qualifier": "organization", "schema": "dc"}, {"key": "dc.contributor.organization", "value": "Jyv\u00e4skyl\u00e4n yliopisto", "language": "fi", "element": "contributor", "qualifier": "organization", "schema": "dc"}, 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