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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><nlm:aff id="A1">Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA</nlm:aff>
</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><nlm:aff id="A1">Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
<affiliation><nlm:aff id="A2">Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</nlm:aff>
</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>
</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><nlm:aff id="A1">Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA</nlm:aff>
</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><nlm:aff id="A1">Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
<affiliation><nlm:aff id="A2">Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium</nlm:aff>
</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
||GM</contract-num>
<contract-num rid="GM1">R01 GM068012-03
||GM</contract-num>
<contract-num rid="GM1">R01 GM068012-02
||GM</contract-num>
<contract-num rid="GM1">R01 GM068012-01
||GM</contract-num>
<contract-sponsor id="GM1">National Institute of General Medical Sciences : NIGMS</contract-sponsor>
</article-meta>
</front>
</pmc>
</record>
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