Enantioselective syntheses of carbocyclic nuleosides 5′-homocarbovir, epi-4′-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations
Identifieur interne : 000641 ( Pmc/Curation ); précédent : 000640; suivant : 000642Enantioselective syntheses of carbocyclic nuleosides 5′-homocarbovir, epi-4′-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations
Auteurs : Lawrence P. Tardibono [États-Unis] ; Marvin J. Miller [États-Unis] ; Jan Balzarini [Belgique]Source :
- Tetrahedron [ 0040-4020 ] ; 2011.
Abstract
Carbocyclic nucleosides (−)-5′-homocarbovir and (+)-
Url:
DOI: 10.1016/j.tet.2010.11.097
PubMed: 21399715
PubMed Central: 3050557
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Enantioselective syntheses of carbocyclic nuleosides 5′-homocarbovir, <italic>epi</italic>-4′-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations</title><author><name sortKey="Tardibono, Lawrence P" sort="Tardibono, Lawrence P" uniqKey="Tardibono L" first="Lawrence P." last="Tardibono">Lawrence P. Tardibono</name><affiliation wicri:level="1"><nlm:aff id="A1">Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556</wicri:regionArea></affiliation></author><author><name sortKey="Miller, Marvin J" sort="Miller, Marvin J" uniqKey="Miller M" first="Marvin J." last="Miller">Marvin J. Miller</name><affiliation wicri:level="1"><nlm:aff id="A1">Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556</wicri:regionArea></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation wicri:level="1"><nlm:aff id="A2">Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">21399715</idno><idno type="pmc">3050557</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050557</idno><idno type="RBID">PMC:3050557</idno><idno type="doi">10.1016/j.tet.2010.11.097</idno><date when="2011">2011</date><idno type="wicri:Area/Pmc/Corpus">000641</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000641</idno><idno type="wicri:Area/Pmc/Curation">000641</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000641</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Enantioselective syntheses of carbocyclic nuleosides 5′-homocarbovir, <italic>epi</italic>-4′-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations</title><author><name sortKey="Tardibono, Lawrence P" sort="Tardibono, Lawrence P" uniqKey="Tardibono L" first="Lawrence P." last="Tardibono">Lawrence P. Tardibono</name><affiliation wicri:level="1"><nlm:aff id="A1">Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556</wicri:regionArea></affiliation></author><author><name sortKey="Miller, Marvin J" sort="Miller, Marvin J" uniqKey="Miller M" first="Marvin J." last="Miller">Marvin J. Miller</name><affiliation wicri:level="1"><nlm:aff id="A1">Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556</wicri:regionArea></affiliation></author><author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name><affiliation wicri:level="1"><nlm:aff id="A2">Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven</wicri:regionArea></affiliation></author></analytic><series><title level="j">Tetrahedron</title><idno type="ISSN">0040-4020</idno><imprint><date when="2011">2011</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p id="P1">Carbocyclic nucleosides (−)-5′-homocarbovir and (+)-<italic>epi</italic>-4′-homocarbovir were prepared from an acylnitroso-derived hetero Diels–Alder cycloadduct. A kinetic enzymatic resolution generated an enantiopure aminocyclopentenol and Pd(0)-mediated decarboxylative allylations of allyl 2,2,2-trifluoroethyl malonates were used to install the 4′-hydroxyethyl groups. Late stage derivatization gave access to the cyclopropylamine congenors, (−)-5′-homoabacavir and (+)-<italic>epi</italic>-4′-homoabacavir. All carbonucleoside target molecules were evaluated for antiviral activity.</p></div></front></TEI><pmc article-type="research-article" xml:lang="EN"><pmc-comment>The publisher of this article does not allow downloading of the full text in XML form.</pmc-comment>
<pmc-dir>properties manuscript</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-journal-id">2984170R</journal-id><journal-id journal-id-type="pubmed-jr-id">7706</journal-id><journal-id journal-id-type="nlm-ta">Tetrahedron</journal-id><journal-title>Tetrahedron</journal-title><issn pub-type="ppub">0040-4020</issn></journal-meta><article-meta><article-id pub-id-type="pmid">21399715</article-id><article-id pub-id-type="pmc">3050557</article-id><article-id pub-id-type="doi">10.1016/j.tet.2010.11.097</article-id><article-id pub-id-type="manuscript">NIHMS261155</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Enantioselective syntheses of carbocyclic nuleosides 5′-homocarbovir, <italic>epi</italic>-4′-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Tardibono</surname><given-names>Lawrence P.</given-names><suffix>Jr.</suffix></name><xref rid="A1" ref-type="aff">a</xref></contrib><contrib contrib-type="author"><name><surname>Miller</surname><given-names>Marvin J.</given-names></name><xref rid="A1" ref-type="aff">a</xref><xref rid="FN1" ref-type="author-notes">*</xref></contrib><contrib contrib-type="author"><name><surname>Balzarini</surname><given-names>Jan</given-names></name><xref rid="A2" ref-type="aff">b</xref></contrib></contrib-group><aff id="A1"><label>a</label>Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA</aff><aff id="A2"><label>b</label>Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</aff><author-notes><corresp id="FN1"><label>*</label>Corresponding author. Tel.: +1-574-631-7571; fax: +1-574-631-6652; <email>mmiller1@nd.edu</email></corresp></author-notes><pub-date pub-type="nihms-submitted"><day>19</day><month>1</month><year>2011</year></pub-date><pub-date pub-type="ppub"><day>4</day><month>2</month><year>2011</year></pub-date><pub-date pub-type="pmc-release"><day>4</day><month>2</month><year>2012</year></pub-date><volume>67</volume><issue>5</issue><fpage>825</fpage><lpage>829</lpage><abstract><p id="P1">Carbocyclic nucleosides (−)-5′-homocarbovir and (+)-<italic>epi</italic>-4′-homocarbovir were prepared from an acylnitroso-derived hetero Diels–Alder cycloadduct. A kinetic enzymatic resolution generated an enantiopure aminocyclopentenol and Pd(0)-mediated decarboxylative allylations of allyl 2,2,2-trifluoroethyl malonates were used to install the 4′-hydroxyethyl groups. Late stage derivatization gave access to the cyclopropylamine congenors, (−)-5′-homoabacavir and (+)-<italic>epi</italic>-4′-homoabacavir. All carbonucleoside target molecules were evaluated for antiviral activity.</p></abstract><contract-num rid="GM1">R01 GM068012-04
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