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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>
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