Enantioselective synthesis of (+)-royleanone from sulfinyl quinones.
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.
Carreño
M C
MC
Departamento de Química Orgánica C-I, Universidad Autónoma, Madrid, Spain. carmen.carrenno@uam.es
García Ruano
J L
JL
Toledo
M A
MA
D045784:Abietanes; D004224:Diterpenes / Q000138:chemical synthesis*; D011809:Quinones / Q000737:chemistry; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry
D045784:Abietanes; D004224:Diterpenes; D011809:Quinones; D013441:Sulfinic Acids; C103399:royleanone