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Enantioselective Synthesis of (+)-Royleanone from Sulfinyl Quinones

✍ Scribed by M. Carmen Carreño; José L. García Ruano; Miguel A. Toledo

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
111 KB
Volume
6
Category
Article
ISSN
0947-6539

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✦ Synopsis

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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