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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Toward the Synthesis of Antascomicin B. Synthesis of a Model of the C22-C34 Fragment via Ireland-Claisen and Allylic Diazene Rearrangements</title><author><name sortKey="Qi, Wei" sort="Qi, Wei" uniqKey="Qi W" first="Wei" last="Qi">Wei Qi</name></author><author><name sortKey="Mcintosh, Matthias C" sort="Mcintosh, Matthias C" uniqKey="Mcintosh M" first="Matthias C." last="Mcintosh">Matthias C. Mcintosh</name></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">19132139</idno><idno type="pmc">2614681</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2614681</idno><idno type="RBID">PMC:2614681</idno><idno type="doi">10.1016/j.tet.2008.05.070</idno><date when="2008">2008</date><idno type="wicri:Area/Pmc/Corpus">000110</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000110</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Toward the Synthesis of Antascomicin B. Synthesis of a Model of the C22-C34 Fragment via Ireland-Claisen and Allylic Diazene Rearrangements</title><author><name sortKey="Qi, Wei" sort="Qi, Wei" uniqKey="Qi W" first="Wei" last="Qi">Wei Qi</name></author><author><name sortKey="Mcintosh, Matthias C" sort="Mcintosh, Matthias C" uniqKey="Mcintosh M" first="Matthias C." last="Mcintosh">Matthias C. Mcintosh</name></author></analytic><series><title level="j">Tetrahedron</title><idno type="ISSN">0040-4020</idno><imprint><date when="2008">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p id="P1">The C22-C34 fragment of antascomicin B lacking the C31 and C32 hydroxyl groups has been prepared in 11 steps from commercially available 2-OH-cyclohexanone. An Ireland-Claisen rearrangement was employed to install the C26 and C27 stereocenters. Our recently reported diastereoselective acyclic 1,3-reductive transposition was used to establish the remote C23 stereocenter. Directed hydrogenation was employed to set the C29 stereocenter. The model compound contains 5 of the stereocenters and all of the carbons of the corresponding fragment of antascomicin B.</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">19132139</article-id><article-id pub-id-type="pmc">2614681</article-id><article-id pub-id-type="doi">10.1016/j.tet.2008.05.070</article-id><article-id pub-id-type="manuscript">NIHMS82752</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 Antascomicin B. Synthesis of a Model of the C22-C34 Fragment via Ireland-Claisen and Allylic Diazene Rearrangements</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Qi</surname><given-names>Wei</given-names></name></contrib><contrib contrib-type="author"><name><surname>McIntosh</surname><given-names>Matthias C.</given-names></name></contrib><aff id="A1">Dept. of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701</aff></contrib-group><pub-date pub-type="nihms-submitted"><day>15</day><month>12</month><year>2008</year></pub-date><pub-date pub-type="ppub"><year>2008</year></pub-date><pub-date pub-type="pmc-release"><day>7</day><month>1</month><year>2009</year></pub-date><volume>64</volume><issue>29</issue><fpage>7021</fpage><lpage>7025</lpage><abstract><p id="P1">The C22-C34 fragment of antascomicin B lacking the C31 and C32 hydroxyl groups has been prepared in 11 steps from commercially available 2-OH-cyclohexanone. An Ireland-Claisen rearrangement was employed to install the C26 and C27 stereocenters. Our recently reported diastereoselective acyclic 1,3-reductive transposition was used to establish the remote C23 stereocenter. Directed hydrogenation was employed to set the C29 stereocenter. The model compound contains 5 of the stereocenters and all of the carbons of the corresponding fragment of antascomicin B.</p></abstract><contract-num rid="CA1">R15 CA125602-01</contract-num><contract-num rid="RR1">P20 RR015569-09</contract-num><contract-sponsor id="CA1">National Cancer Institute : NCI</contract-sponsor><contract-sponsor id="RR1">National Center for Research Resources : NCRR</contract-sponsor></article-meta></front></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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