title: An enantioselective approach to furanoeremophilanes: (+)-9-oxoeuryopsin.
abstract: An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin 1 is reported. The synthesis involves as a key step a copper(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe3 to 2-methyl-2-cyclohexen-1-one with the Feringa (S,R,R)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde 4. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis.
authors: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, México DF 04510, Mexico.
authors: Ana L
authors: AL
authors: Silva
authors: Rubén A
authors: RA
authors: Toscano
authors: Luis A
authors: LA
authors: Maldonado
mesh_terms: D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C584176:9-oxoeuryopsin; D012717:Sesquiterpenes