First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol.
[reaction: see text] A new route toward puupehenone-related bioactive metabolites from (-)-sclareol, based on the palladium(II)-mediated diastereoselective cyclization of a drimenylphenol, is described. Utilizing this, the first enantiospecific synthesis of the antitumor and antimalarial (-)-15-oxopuupehenol, together with improved syntheses of (+)-puupehenone, (+)-puupehedione, and (+)-15-cyanopuupehenone, were accomplished.
Alvarez-Manzaneda
E J
EJ
Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain. eamr@ugr.es
Chahboun
R
R
Barranco Pérez
I
I
Cabrera
E
E
Alvarez
E
E
Alvarez-Manzaneda
R
R
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D044004:Xanthones / Q000138:chemical synthesis / Q000737:chemistry*
C507449:15-oxopuupehenol; D000962:Antimalarials; D000970:Antineoplastic Agents; D004224:Diterpenes; D012717:Sesquiterpenes; D044004:Xanthones; C053594:puupehenone; C070760:sclareol