Related Experiment Videos
Enantioselective synthesis of (+)-royleanone from sulfinyl quinones
M C Carreño1, J L García Ruano, M A Toledo
1Departamento de Química Orgánica C-I, Universidad Autónoma, Madrid, Spain. carmen.carrenno@uam.es
Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 5, 2002
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.