Enantioselective synthesis of (+)-royleanone from sulfinyl quinones |
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Authors: | Carreño M C García Ruano J L Toledo M A |
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Institution: | Departamento de Química Orgánica C-I, Universidad Autónoma, Madrid, Spain. carmen.carrenno@uam.es |
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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. |
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