A domino N-amidoacylation/aldol-type condensation approach to the synthesis of the topo-I inhibitor Rosettacin and derivatives.
Identifieur interne : 000259 ( PubMed/Checkpoint ); précédent : 000258; suivant : 000260A 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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pubmed:18254644Le document en format XML
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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><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">18254644</PMID><DateCreated><Year>2008</Year><Month>3</Month><Day>3</Day></DateCreated><DateCompleted><Year>2008</Year><Month>05</Month><Day>14</Day></DateCompleted><DateRevised><Year>2010</Year><Month>11</Month><Day>18</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">0022-3263</ISSN><JournalIssue CitedMedium="Print"><Volume>73</Volume><Issue>5</Issue><PubDate><Year>2008</Year><Month>Mar</Month><Day>7</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>A domino N-amidoacylation/aldol-type condensation approach to the synthesis of the topo-I inhibitor Rosettacin and derivatives.</ArticleTitle><Pagination><MedlinePgn>1975-8</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo702387q</ELocationID><Abstract><AbstractText>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. 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