First synthesis of antitumoral dasyscyphin B

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URI: http://hdl.handle.net/10481/27971
ISSN: 1477-0520
ISSN: 1477-0539
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Auteur
Akhaouzan, Ali; Fernández, Antonio; Mansour, Ahmed I.; Álvarez, Esteban; Haidour, Ali; Álvarez-Manzaneda, Ramón; Chahboun Karimi, Rachid; Álvarez-Manzaneda, Enrique
Editorial
Royal Society of Chemistry
Materia
Antitumoral
 
Dasyscyphus niveus
 
Date
2013-07-23
Referencia bibliográfica
Akhaouzan, A.; et al. First synthesis of antitumoral dasyscyphin B. Organic and Biomolecular Chemistry, 11(36): 6176-6185 (2013). [http://hdl.handle.net/10481/27971]
Patrocinador
The authors thank the Spanish Ministry of Science and Innovation (project CTQ2009-09932) and the Regional Government of Andalucia (project P11-CTS-7651 and assistance to the FQM-348 group) for financial support. A.F. thanks the Spanish Ministry of Science and Innovation for the predoctoral grant provided.
Résumé
The first synthesis of dasyscyphin B, an antitumoral metabolite obtained from the ascomycete Dasyscyphus niveus, has been achieved starting from commercial abietic acid. The key steps of the synthetic sequence are the diastereoselective α-methylation of a ketoaldehyde, followed by an intramolecular aldol condensation and the further Diels–Alder cycloaddition of a dienol ester. The procedure reported will allow the synthesis of related metabolites functionalized in the A ring.
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