Spiroacetal Formation through Telescoped Cycloaddition and Carbon–Hydrogen Bond Functionalization: Total Synthesis of Bistramide A
Identifieur interne : 000E12 ( Pmc/Curation ); précédent : 000E11; suivant : 000E13Spiroacetal Formation through Telescoped Cycloaddition and Carbon–Hydrogen Bond Functionalization: Total Synthesis of Bistramide A
Auteurs : Xun Han ; Paul E. FloreancigSource :
- Angewandte Chemie (International ed. in English) [ 1433-7851 ] ; 2014.
Abstract
Spiroacetals can be formed through a one-pot sequence of a hetero Diels-Alder reaction, an oxidative carbon–hydrogen bond cleavage, and an acid treatment. This convergent approach expedites access to a complex molecular subunit that is present in numerous biologically active structures. The utility of the protocol is demonstrated through its application to a brief synthesis of the actin-binding cytotoxin bistramide A.
Url:
DOI: 10.1002/anie.201406819
PubMed: 25196585
PubMed Central: 4234310
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Spiroacetal Formation through Telescoped Cycloaddition and Carbon–Hydrogen Bond Functionalization: Total Synthesis of Bistramide A</title><author><name sortKey="Han, Xun" sort="Han, Xun" uniqKey="Han X" first="Xun" last="Han">Xun Han</name></author><author><name sortKey="Floreancig, Paul E" sort="Floreancig, Paul E" uniqKey="Floreancig P" first="Paul E." last="Floreancig">Paul E. Floreancig</name></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">25196585</idno><idno type="pmc">4234310</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4234310</idno><idno type="RBID">PMC:4234310</idno><idno type="doi">10.1002/anie.201406819</idno><date when="2014">2014</date><idno type="wicri:Area/Pmc/Corpus">000E37</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000E37</idno><idno type="wicri:Area/Pmc/Curation">000E12</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000E12</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Spiroacetal Formation through Telescoped Cycloaddition and Carbon–Hydrogen Bond Functionalization: Total Synthesis of Bistramide A</title><author><name sortKey="Han, Xun" sort="Han, Xun" uniqKey="Han X" first="Xun" last="Han">Xun Han</name></author><author><name sortKey="Floreancig, Paul E" sort="Floreancig, Paul E" uniqKey="Floreancig P" first="Paul E." last="Floreancig">Paul E. Floreancig</name></author></analytic><series><title level="j">Angewandte Chemie (International ed. in English)</title><idno type="ISSN">1433-7851</idno><idno type="eISSN">1521-3773</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p id="P1">Spiroacetals can be formed through a one-pot sequence of a hetero Diels-Alder reaction, an oxidative carbon–hydrogen bond cleavage, and an acid treatment. This convergent approach expedites access to a complex molecular subunit that is present in numerous biologically active structures. The utility of the protocol is demonstrated through its application to a brief synthesis of the actin-binding cytotoxin bistramide A.</p></div></front></TEI><pmc article-type="research-article"><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">0370543</journal-id><journal-id journal-id-type="pubmed-jr-id">537</journal-id><journal-id journal-id-type="nlm-ta">Angew Chem Int Ed Engl</journal-id><journal-id journal-id-type="iso-abbrev">Angew. Chem. Int. Ed. Engl.</journal-id><journal-title-group><journal-title>Angewandte Chemie (International ed. in English)</journal-title></journal-title-group><issn pub-type="ppub">1433-7851</issn><issn pub-type="epub">1521-3773</issn></journal-meta><article-meta><article-id pub-id-type="pmid">25196585</article-id><article-id pub-id-type="pmc">4234310</article-id><article-id pub-id-type="doi">10.1002/anie.201406819</article-id><article-id pub-id-type="manuscript">NIHMS637149</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Spiroacetal Formation through Telescoped Cycloaddition and Carbon–Hydrogen Bond Functionalization: Total Synthesis of Bistramide A</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Han</surname><given-names>Xun</given-names></name></contrib><contrib contrib-type="author"><name><surname>Floreancig</surname><given-names>Paul E.</given-names><prefix>Prof.</prefix></name><xref ref-type="corresp" rid="CR1">*</xref></contrib><aff id="A1">Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA)</aff></contrib-group><author-notes><corresp id="CR1"><label>*</label>Fax: (+)1-412-624-8611, <email>florean@pitt.edu</email></corresp></author-notes><pub-date pub-type="nihms-submitted"><day>8</day><month>11</month><year>2014</year></pub-date><pub-date pub-type="epub"><day>04</day><month>9</month><year>2014</year></pub-date><pub-date pub-type="ppub"><day>6</day><month>10</month><year>2014</year></pub-date><pub-date pub-type="pmc-release"><day>06</day><month>10</month><year>2015</year></pub-date><volume>53</volume><issue>41</issue><fpage>11075</fpage><lpage>11078</lpage><pmc-comment>elocation-id from pubmed: 10.1002/anie.201406819</pmc-comment>
<permissions><copyright-statement>© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</copyright-statement><copyright-year>2013</copyright-year></permissions><abstract><p id="P1">Spiroacetals can be formed through a one-pot sequence of a hetero Diels-Alder reaction, an oxidative carbon–hydrogen bond cleavage, and an acid treatment. This convergent approach expedites access to a complex molecular subunit that is present in numerous biologically active structures. The utility of the protocol is demonstrated through its application to a brief synthesis of the actin-binding cytotoxin bistramide A.</p></abstract><kwd-group><kwd>cycloaddition</kwd><kwd>C–H activation</kwd><kwd>spiro compound</kwd><kwd>natural products</kwd><kwd>stereoselectivity</kwd></kwd-group></article-meta></front></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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