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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Asymmetric Total Synthesis of (+)- and (−)-Clusianone and (+)- and (−)Clusianone Methyl Enol Ether via ACC Alkylation and Evaluation of their Anti-HIV Activity</title><author><name sortKey="Garnsey, Michelle R" sort="Garnsey, Michelle R" uniqKey="Garnsey M" first="Michelle R." last="Garnsey">Michelle R. Garnsey</name><affiliation><nlm:aff id="A1">Department of Chemistry, Duke University, Durham, North Carolina, 27705, USA</nlm:aff></affiliation></author><author><name sortKey="Matous, James A" sort="Matous, James A" uniqKey="Matous J" first="James A." last="Matous">James A. Matous</name><affiliation><nlm:aff id="A2">Department of Microbiology and the Division of Infectious Diseases, The Ohio State University, Columbus, Ohio, 43210, USA</nlm:aff></affiliation></author><author><name sortKey="Kwiek, Jesse J" sort="Kwiek, Jesse J" uniqKey="Kwiek J" first="Jesse J." last="Kwiek">Jesse J. Kwiek</name><affiliation><nlm:aff id="A2">Department of Microbiology and the Division of Infectious Diseases, The Ohio State University, Columbus, Ohio, 43210, USA</nlm:aff></affiliation></author><author><name sortKey="Coltart, Don M" sort="Coltart, Don M" uniqKey="Coltart D" first="Don M." last="Coltart">Don M. Coltart</name><affiliation><nlm:aff id="A1">Department of Chemistry, Duke University, Durham, North Carolina, 27705, USA</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">21414776</idno><idno type="pmc">3070777</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3070777</idno><idno type="RBID">PMC:3070777</idno><idno type="doi">10.1016/j.bmcl.2011.02.074</idno><date when="2011">2011</date><idno type="wicri:Area/Pmc/Corpus">000112</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000112</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Asymmetric Total Synthesis of (+)- and (−)-Clusianone and (+)- and (−)Clusianone Methyl Enol Ether via ACC Alkylation and Evaluation of their Anti-HIV Activity</title><author><name sortKey="Garnsey, Michelle R" sort="Garnsey, Michelle R" uniqKey="Garnsey M" first="Michelle R." last="Garnsey">Michelle R. Garnsey</name><affiliation><nlm:aff id="A1">Department of Chemistry, Duke University, Durham, North Carolina, 27705, USA</nlm:aff></affiliation></author><author><name sortKey="Matous, James A" sort="Matous, James A" uniqKey="Matous J" first="James A." last="Matous">James A. Matous</name><affiliation><nlm:aff id="A2">Department of Microbiology and the Division of Infectious Diseases, The Ohio State University, Columbus, Ohio, 43210, USA</nlm:aff></affiliation></author><author><name sortKey="Kwiek, Jesse J" sort="Kwiek, Jesse J" uniqKey="Kwiek J" first="Jesse J." last="Kwiek">Jesse J. Kwiek</name><affiliation><nlm:aff id="A2">Department of Microbiology and the Division of Infectious Diseases, The Ohio State University, Columbus, Ohio, 43210, USA</nlm:aff></affiliation></author><author><name sortKey="Coltart, Don M" sort="Coltart, Don M" uniqKey="Coltart D" first="Don M." last="Coltart">Don M. Coltart</name><affiliation><nlm:aff id="A1">Department of Chemistry, Duke University, Durham, North Carolina, 27705, USA</nlm:aff></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="ISSN">0960-894X</idno><idno type="eISSN">1464-3405</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">The total asymmetric synthesis of (+)- and (−)-clusianone and (+)- and (−)-clusianone methyl enol ether is reported. Asymmetric induction is achieved through the use of ACC alkylation, providing the key intermediates with an <italic>er</italic> of 99:1. The four synthetic compounds were evaluated for their anti-HIV activity. Both (+)- and (−)-clusianone displayed significant anti-HIV activity.</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">9107377</journal-id><journal-id journal-id-type="pubmed-jr-id">20409</journal-id><journal-id journal-id-type="nlm-ta">Bioorg Med Chem Lett</journal-id><journal-title>Bioorganic & medicinal chemistry letters</journal-title><issn pub-type="ppub">0960-894X</issn><issn pub-type="epub">1464-3405</issn></journal-meta><article-meta><article-id pub-id-type="pmid">21414776</article-id><article-id pub-id-type="pmc">3070777</article-id><article-id pub-id-type="doi">10.1016/j.bmcl.2011.02.074</article-id><article-id pub-id-type="manuscript">NIHMS277158</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Asymmetric Total Synthesis of (+)- and (−)-Clusianone and (+)- and (−)Clusianone Methyl Enol Ether via ACC Alkylation and Evaluation of their Anti-HIV Activity</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Garnsey</surname><given-names>Michelle R.</given-names></name><xref ref-type="aff" rid="A1">a</xref></contrib><contrib contrib-type="author"><name><surname>Matous</surname><given-names>James A.</given-names></name><xref ref-type="aff" rid="A2">b</xref></contrib><contrib contrib-type="author"><name><surname>Kwiek</surname><given-names>Jesse J.</given-names></name><xref ref-type="aff" rid="A2">b</xref></contrib><contrib contrib-type="author"><name><surname>Coltart</surname><given-names>Don M.</given-names></name><xref ref-type="aff" rid="A1">a</xref></contrib></contrib-group><aff id="A1"><label>a</label>Department of Chemistry, Duke University, Durham, North Carolina, 27705, USA</aff><aff id="A2"><label>b</label>Department of Microbiology and the Division of Infectious Diseases, The Ohio State University, Columbus, Ohio, 43210, USA</aff><pub-date pub-type="nihms-submitted"><day>3</day><month>3</month><year>2011</year></pub-date><pub-date pub-type="epub"><day>23</day><month>2</month><year>2011</year></pub-date><pub-date pub-type="ppub"><day>15</day><month>4</month><year>2011</year></pub-date><pub-date pub-type="pmc-release"><day>15</day><month>4</month><year>2012</year></pub-date><volume>21</volume><issue>8</issue><fpage>2406</fpage><lpage>2409</lpage><permissions><copyright-statement>© 2011 Elsevier Ltd. All rights reserved.</copyright-statement><copyright-year>2011</copyright-year></permissions><abstract><p id="P1">The total asymmetric synthesis of (+)- and (−)-clusianone and (+)- and (−)-clusianone methyl enol ether is reported. Asymmetric induction is achieved through the use of ACC alkylation, providing the key intermediates with an <italic>er</italic> of 99:1. The four synthetic compounds were evaluated for their anti-HIV activity. Both (+)- and (−)-clusianone displayed significant anti-HIV activity.</p></abstract><kwd-group><kwd>ACC ketone alkylation</kwd><kwd>Asymmetric synthesis</kwd><kwd>Polycyclic polyprenylated acylphloroglucinols</kwd><kwd>Viral infection</kwd><kwd>Anti-HIV activity</kwd></kwd-group><contract-num rid="AI1">R01 AI090644-01
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