A domino N-amidoacylation/aldol-type condensation approach to the synthesis of the topo-I inhibitor Rosettacin and derivatives.
Identifieur interne : 000D57 ( Main/Exploration ); précédent : 000D56; suivant : 000D58A domino N-amidoacylation/aldol-type condensation approach to the synthesis of the topo-I inhibitor Rosettacin and derivatives.
Auteurs : Frédéric Pin [France] ; Sébastien Comesse ; Morgane Sanselme ; Adam DaïchSource :
- The Journal of organic chemistry [ 0022-3263 ] ; 2008.
English descriptors
- KwdEn :
- Acylation, Enzyme Inhibitors (chemical synthesis), Enzyme Inhibitors (chemistry), Enzyme Inhibitors (pharmacology), Heterocyclic Compounds with 4 or More Rings (chemical synthesis), Heterocyclic Compounds with 4 or More Rings (chemistry), Heterocyclic Compounds with 4 or More Rings (pharmacology), Topoisomerase I Inhibitors.
- MESH :
- chemical , chemical synthesis : Enzyme Inhibitors, Heterocyclic Compounds with 4 or More Rings.
- chemical , chemistry : Enzyme Inhibitors, Heterocyclic Compounds with 4 or More Rings.
- chemical , pharmacology : Enzyme Inhibitors, Heterocyclic Compounds with 4 or More Rings.
- Acylation, Topoisomerase I Inhibitors.
Abstract
The pot, atom, and step-economic synthesis of Rosettacin topo-I poison and its derivatives has been achieved using a novel domino N-amidoacylation/aldol-type condensation, followed by decarboxylation of the ester function. The key domino procedure simply involves mixing HOBt ester as new reagent with lactam and NaH together in THF or THF/ DMF. The reaction seems to be general and led to suitable N-heterocyclic products in moderate to good yields.
DOI: 10.1021/jo702387q
PubMed: 18254644
Affiliations:
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Le document en format XML
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sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name></author><author><name sortKey="Sanselme, Morgane" sort="Sanselme, Morgane" uniqKey="Sanselme M" first="Morgane" last="Sanselme">Morgane Sanselme</name></author><author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2008">2008</date><idno type="RBID">pubmed:18254644</idno><idno type="pmid">18254644</idno><idno type="doi">10.1021/jo702387q</idno><idno type="wicri:Area/PubMed/Corpus">000259</idno><idno type="wicri:Area/PubMed/Curation">000259</idno><idno type="wicri:Area/PubMed/Checkpoint">000259</idno><idno type="wicri:Area/Ncbi/Merge">000202</idno><idno type="wicri:Area/Ncbi/Curation">000202</idno><idno type="wicri:Area/Ncbi/Checkpoint">000202</idno><idno type="wicri:doubleKey">0022-3263:2008:Pin 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(chemistry)</term><term>Enzyme Inhibitors (pharmacology)</term><term>Heterocyclic Compounds with 4 or More Rings (chemical synthesis)</term><term>Heterocyclic Compounds with 4 or More Rings (chemistry)</term><term>Heterocyclic Compounds with 4 or More Rings (pharmacology)</term><term>Topoisomerase I Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Enzyme Inhibitors</term><term>Heterocyclic Compounds with 4 or More Rings</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Enzyme Inhibitors</term><term>Heterocyclic Compounds with 4 or More Rings</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Enzyme Inhibitors</term><term>Heterocyclic Compounds with 4 or More Rings</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Acylation</term><term>Topoisomerase I Inhibitors</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The pot, atom, and step-economic synthesis of Rosettacin topo-I poison and its derivatives has been achieved using a novel domino N-amidoacylation/aldol-type condensation, followed by decarboxylation of the ester function. The key domino procedure simply involves mixing HOBt ester as new reagent with lactam and NaH together in THF or THF/ DMF. The reaction seems to be general and led to suitable N-heterocyclic products in moderate to good yields.</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li></region><settlement><li>Le Havre</li></settlement><orgName><li>Université du Havre</li></orgName></list><tree><noCountry><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name><name sortKey="Sanselme, Morgane" sort="Sanselme, Morgane" uniqKey="Sanselme M" first="Morgane" last="Sanselme">Morgane Sanselme</name></noCountry><country name="France"><region name="Région Normandie"><name sortKey="Pin, Frederic" sort="Pin, Frederic" uniqKey="Pin F" first="Frédéric" last="Pin">Frédéric Pin</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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