CovidV2, Main, Exploration, bibRecord, 001403

Enantioselective syntheses of carbocyclic nuleosides 5′-homocarbovir, epi-4′-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations

Identifieur interne : 001403 ( Main/Exploration ); précédent : 001402; suivant : 001404

Enantioselective 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.

RBID : PMC:3050557

Abstract

Carbocyclic nucleosides (−)-5′-homocarbovir and (+)-epi-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 (+)-epi-4′-homoabacavir. All carbonucleoside target molecules were evaluated for antiviral activity.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3050557

DOI: 10.1016/j.tet.2010.11.097
PubMed: 21399715
PubMed Central: 3050557

Affiliations:

Le document en format XML

<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="2"><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>
<placeName><region type="state">Indiana</region>
</placeName>
</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="2"><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>
<placeName><region type="state">Indiana</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
<affiliation wicri:level="4"><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>
<orgName type="university">Katholieke Universiteit Leuven</orgName>
<placeName><settlement type="city">Louvain</settlement>
<region>Région flamande</region>
<region type="district" nuts="2">Province du Brabant flamand</region>
</placeName>
</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>
<idno type="wicri:Area/Pmc/Checkpoint">000812</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000812</idno>
<idno type="wicri:Area/Ncbi/Merge">000253</idno>
<idno type="wicri:Area/Ncbi/Curation">000253</idno>
<idno type="wicri:Area/Ncbi/Checkpoint">000253</idno>
<idno type="wicri:doubleKey">0040-4020:2011:Tardibono L:enantioselective:syntheses:of</idno>
<idno type="wicri:Area/Main/Merge">001405</idno>
<idno type="wicri:Area/Main/Curation">001403</idno>
<idno type="wicri:Area/Main/Exploration">001403</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="2"><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>
<placeName><region type="state">Indiana</region>
</placeName>
</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="2"><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>
<placeName><region type="state">Indiana</region>
</placeName>
</affiliation>
</author>
<author><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
<affiliation wicri:level="4"><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>
<orgName type="university">Katholieke Universiteit Leuven</orgName>
<placeName><settlement type="city">Louvain</settlement>
<region>Région flamande</region>
<region type="district" nuts="2">Province du Brabant flamand</region>
</placeName>
</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>
<affiliations><list><country><li>Belgique</li>
<li>États-Unis</li>
</country>
<region><li>Indiana</li>
<li>Province du Brabant flamand</li>
<li>Région flamande</li>
</region>
<settlement><li>Louvain</li>
</settlement>
<orgName><li>Katholieke Universiteit Leuven</li>
</orgName>
</list>
<tree><country name="États-Unis"><region name="Indiana"><name sortKey="Tardibono, Lawrence P" sort="Tardibono, Lawrence P" uniqKey="Tardibono L" first="Lawrence P." last="Tardibono">Lawrence P. Tardibono</name>
</region>
<name sortKey="Miller, Marvin J" sort="Miller, Marvin J" uniqKey="Miller M" first="Marvin J." last="Miller">Marvin J. Miller</name>
</country>
<country name="Belgique"><region name="Région flamande"><name sortKey="Balzarini, Jan" sort="Balzarini, Jan" uniqKey="Balzarini J" first="Jan" last="Balzarini">Jan Balzarini</name>
</region>
</country>
</tree>
</affiliations>
</record>

Pour manipuler ce document sous Unix (Dilib)

EXPLOR_STEP=$WICRI_ROOT/Wicri/Sante/explor/CovidV2/Data/Main/Exploration

HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 001403 | SxmlIndent | more

HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 001403 | SxmlIndent | more

Pour mettre un lien sur cette page dans le réseau Wicri

{{Explor lien
   |wiki=    Wicri/Sante
   |area=    CovidV2
   |flux=    Main
   |étape=   Exploration
   |type=    RBID
   |clé=     PMC:3050557
   |texte=   Enantioselective syntheses of carbocyclic nuleosides 5′-homocarbovir, epi-4′-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations
}}

Pour générer des pages wiki

HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Exploration/RBID.i   -Sk "pubmed:21399715" \
       | HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd   \
       | NlmPubMed2Wicri -a CovidV2

This area was generated with Dilib version V0.6.33.
Data generation: Sat Mar 28 17:51:24 2020. Site generation: Sun Jan 31 15:35:48 2021

Serveur d'exploration Covid (26 mars)

Enantioselective syntheses of carbocyclic nuleosides 5′-homocarbovir, epi-4′-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations

Enantioselective syntheses of carbocyclic nuleosides 5′-homocarbovir, epi-4′-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations

Source :

Abstract

Links toward previous steps (curation, corpus...)

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri

Pour générer des pages wiki

	Serveur d'exploration Covid (26 mars)
	Attention, ce site est en cours de développement ! Attention, site généré par des moyens informatiques à partir de corpus bruts. Les informations ne sont donc pas validées.