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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<author><name sortKey="Han, Xun" sort="Han, Xun" uniqKey="Han X" first="Xun" last="Han">Xun Han</name>
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<author><name sortKey="Floreancig, Paul E" sort="Floreancig, Paul E" uniqKey="Floreancig P" first="Paul E." last="Floreancig">Paul E. Floreancig</name>
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<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>
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<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>
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<article-categories><subj-group subj-group-type="heading"><subject>Article</subject>
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<title-group><article-title>Spiroacetal Formation through Telescoped Cycloaddition and Carbon–Hydrogen Bond Functionalization: Total Synthesis of Bistramide A</article-title>
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<contrib-group><contrib contrib-type="author"><name><surname>Han</surname>
<given-names>Xun</given-names>
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<contrib contrib-type="author"><name><surname>Floreancig</surname>
<given-names>Paul E.</given-names>
<prefix>Prof.</prefix>
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<xref ref-type="corresp" rid="CR1">*</xref>
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<aff id="A1">Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 (USA)</aff>
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<author-notes><corresp id="CR1"><label>*</label>
Fax: (+)1-412-624-8611, <email>florean@pitt.edu</email>
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<pub-date pub-type="nihms-submitted"><day>8</day>
<month>11</month>
<year>2014</year>
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<pub-date pub-type="epub"><day>04</day>
<month>9</month>
<year>2014</year>
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<pub-date pub-type="ppub"><day>6</day>
<month>10</month>
<year>2014</year>
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<pub-date pub-type="pmc-release"><day>06</day>
<month>10</month>
<year>2015</year>
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<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>
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<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>
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<kwd-group><kwd>cycloaddition</kwd>
<kwd>C–H activation</kwd>
<kwd>spiro compound</kwd>
<kwd>natural products</kwd>
<kwd>stereoselectivity</kwd>
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