First synthesis of antitumoral dasyscyphin B.
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.
Laboratoire de Chimie Organique Appliquée, Département de Chimie, Faculté des Sciences, Université Abdelmalek Essaâdi, Tetouan, Morocco.
Ali
A
Akhaouzan
Antonio
A
Fernández
Ahmed I
AI
Mansour
Esteban
E
Alvarez
Ali
A
Haidöur
Ramón
R
Alvarez-Manzaneda
Rachid
R
Chahboun
Enrique
E
Alvarez-Manzaneda
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001203:Ascomycota / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D004224:Diterpenes; C509642:dasyscyphin B