Diels-Alder cycloaddition approach to puupehenone-related metabolites: synthesis of the potent angiogenesis inhibitor 8-epipuupehedione.
A new synthetic strategy toward puupehenone-related bioactive metabolites from sclareol oxide, based on a Diels-Alder cycloaddition approach, is described. Utilizing this, marine ent-chromazonarol and the potent angiogenesis inhibitor 8-epipuupehedione have been synthesized.
Alvarez-Manzaneda
E J
EJ
Departamento de Química OrgAnica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain. eamr@ugr.es
Chahboun
R
R
Cabrera
E
E
Alvarez
E
E
Haidour
A
A
Ramos
J M
JM
Alvarez-Manzaneda
R
R
Hmamouchi
M
M
Bouanou
H
H
D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D012717:Sesquiterpenes / Q000737:chemistry / Q000378:metabolism*; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry; D014966:Xanthenes / Q000138:chemical synthesis; D044004:Xanthones / Q000737:chemistry / Q000378:metabolism*
C481243:8-epipuupehedione; D020533:Angiogenesis Inhibitors; D012717:Sesquiterpenes; D013729:Terpenes; D014966:Xanthenes; D044004:Xanthones; C121655:chromazonarol; C053594:puupehenone