title: Enantioselective synthesis of (+)-royleanone from sulfinyl quinones.
abstract: A convergent enantioselective synthesis of (+)-royleanone (1) is described starting from enantiomerically pure (S)-3-hydroxy-2-isopropyl-5-tert-butylsulfinyl-p-benzoquinone, which is readily available from 3-isopropyl-1,2,4-trimethoxybenzene and 1,3,3-trimethyl-2-vinylcyclohexene. The key step is a tandem asymmetric Diels-Alder reaction/pyrolytic sulfoxide elimination process.
authors.affiliation: Departamento de Química Orgánica C-I, Universidad Autónoma, Madrid, Spain. carmen.carrenno@uam.es
authors.forename: M C
authors.initials: MC
authors.lastname: Carreño
authors.forename: J L
authors.initials: JL
authors.lastname: García Ruano
authors.forename: M A
authors.initials: MA
authors.lastname: Toledo
mesh_terms: D045784:Abietanes; D004224:Diterpenes / Q000138:chemical synthesis*; D011809:Quinones / Q000737:chemistry; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry
chemical_list: D045784:Abietanes; D004224:Diterpenes; D011809:Quinones; D013441:Sulfinic Acids; C103399:royleanone