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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction</title><author><name sortKey="Gazaille, Jeffrey A" sort="Gazaille, Jeffrey A" uniqKey="Gazaille J" first="Jeffrey A." last="Gazaille">Jeffrey A. Gazaille</name></author><author><name sortKey="Abramite, Joseph A" sort="Abramite, Joseph A" uniqKey="Abramite J" first="Joseph A." last="Abramite">Joseph A. Abramite</name></author><author><name sortKey="Sammakia, Tarek" sort="Sammakia, Tarek" uniqKey="Sammakia T" first="Tarek" last="Sammakia">Tarek Sammakia</name></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">22149174</idno><idno type="pmc">3272878</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3272878</idno><idno type="RBID">PMC:3272878</idno><idno type="doi">10.1021/ol202966m</idno><date when="2011">2011</date><idno type="wicri:Area/Pmc/Corpus">000117</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000117</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction</title><author><name sortKey="Gazaille, Jeffrey A" sort="Gazaille, Jeffrey A" uniqKey="Gazaille J" first="Jeffrey A." last="Gazaille">Jeffrey A. Gazaille</name></author><author><name sortKey="Abramite, Joseph A" sort="Abramite, Joseph A" uniqKey="Abramite J" first="Joseph A." last="Abramite">Joseph A. Abramite</name></author><author><name sortKey="Sammakia, Tarek" sort="Sammakia, Tarek" uniqKey="Sammakia T" first="Tarek" last="Sammakia">Tarek Sammakia</name></author></analytic><series><title level="j">Organic Letters</title><idno type="ISSN">1523-7060</idno><idno type="eISSN">1523-7052</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"><graphic xlink:href="nihms344135u1.jpg" position="float" orientation="portrait"></graphic></p><p id="P2">The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A is described. The reaction was applied to compound 19, and proceeds in high yield and good levels of diastereoselectivity. Application of the Achmatowicz reaction to this intermediate provided the corresponding pyranone, a late stage intermediate well positioned for conversion to the natural product.</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">100890393</journal-id><journal-id journal-id-type="pubmed-jr-id">21677</journal-id><journal-id journal-id-type="nlm-ta">Org Lett</journal-id><journal-title-group><journal-title>Organic Letters</journal-title></journal-title-group><issn pub-type="ppub">1523-7060</issn><issn pub-type="epub">1523-7052</issn></journal-meta><article-meta><article-id pub-id-type="pmid">22149174</article-id><article-id pub-id-type="pmc">3272878</article-id><article-id pub-id-type="doi">10.1021/ol202966m</article-id><article-id pub-id-type="manuscript">NIHMS344135</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Gazaille</surname><given-names>Jeffrey A.</given-names></name></contrib><contrib contrib-type="author"><name><surname>Abramite</surname><given-names>Joseph A.</given-names></name></contrib><contrib contrib-type="author"><name><surname>Sammakia</surname><given-names>Tarek</given-names></name><xref rid="FN1" ref-type="author-notes">*</xref></contrib><aff id="A1">Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215</aff></contrib-group><author-notes><corresp id="FN1"><email>sammakia@colorado.edu</email></corresp></author-notes><pub-date pub-type="nihms-submitted"><day>15</day><month>12</month><year>2011</year></pub-date><pub-date pub-type="epub"><day>12</day><month>12</month><year>2011</year></pub-date><pub-date pub-type="ppub"><day>6</day><month>1</month><year>2012</year></pub-date><pub-date pub-type="pmc-release"><day>6</day><month>1</month><year>2013</year></pub-date><volume>14</volume><issue>1</issue><fpage>178</fpage><lpage>181</lpage><abstract><p id="P1"><graphic xlink:href="nihms344135u1.jpg" position="float" orientation="portrait"></graphic></p><p id="P2">The use of the intramolecular vinylogous aldol reaction for the preparation of an advanced intermediate for the synthesis of peloruside A is described. The reaction was applied to compound 19, and proceeds in high yield and good levels of diastereoselectivity. Application of the Achmatowicz reaction to this intermediate provided the corresponding pyranone, a late stage intermediate well positioned for conversion to the natural product.</p></abstract><funding-group><award-group><funding-source country="United States">National Institute of General Medical Sciences : NIGMS</funding-source><award-id>R01 GM048498-14 || GM</award-id></award-group></funding-group></article-meta></front></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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