First enantioselective total synthesis and configurational assignments of suberosenone and suberosanone as potential antitumor agentsElectronic supplementary information (ESI) available. See DOI: 10.1039/c4cc10041g

The first enantioselective total syntheses of two marine sesquiterpenes (1 R )-suberosenone and (1 R )-suberosanone are achieved leading to revision of the AC of natural (1 S )-suberosanone. Key elements of the synthesis include hyperbaric asymmetric Michael addition and highly efficient silver trif...

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Hauptverfasser: Kousara, Mohammad, Ferry, Angélique, Le Bideau, Franck, Serré, Kathalyn L, Chataigner, Isabelle, Morvan, Estelle, Dubois, Joëlle, Chéron, Monique, Dumas, Françoise
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Sprache:eng
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Zusammenfassung:The first enantioselective total syntheses of two marine sesquiterpenes (1 R )-suberosenone and (1 R )-suberosanone are achieved leading to revision of the AC of natural (1 S )-suberosanone. Key elements of the synthesis include hyperbaric asymmetric Michael addition and highly efficient silver trifluoroacetate mediated α-alkylation for the formation of ring A. The first enantioselective syntheses of (1 R )-suberosenone and (1 R )-suberosanone are achieved, leading to revision of the AC of a natural (1 S )-suberosanone.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc10041g