The Friedel−Crafts Allylation of a Prenyl Group Stabilized by a Sulfone Moiety:  Expeditious Syntheses of Ubiquinones and Menaquinones

The Friedel−Crafts Allylation of a Prenyl Group Stabilized by a Sulfone Moiety:  Expeditious Syntheses of Ubiquinones and Menaquinones

An efficient synthetic method for the protected p-hydroquinone compounds 4 containing the C5 trans allylic sulfone moiety has been developed by the direct Friedel−Crafts allylation of the protected dihydroquinone 2 with 4-chloro-2-methyl-1-phenylsulfonyl-2-butene (7a) or 4-hydroxy-2-methyl-1-phenyls...

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Veröffentlicht in:Journal of organic chemistry 2003-10, Vol.68 (20), p.7925-7927
Hauptverfasser: Min, Jae-Hong, Lee, Jun-Sup, Yang, Jae-Deuk, Koo, Sangho
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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Beschreibung
Zusammenfassung:An efficient synthetic method for the protected p-hydroquinone compounds 4 containing the C5 trans allylic sulfone moiety has been developed by the direct Friedel−Crafts allylation of the protected dihydroquinone 2 with 4-chloro-2-methyl-1-phenylsulfonyl-2-butene (7a) or 4-hydroxy-2-methyl-1-phenylsulfonyl-2-butene (7b). Expeditious total syntheses of coenzyme Q-10 and vitamin K2(20) have been demonstrated from these valuable key compounds 4a and 4b.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0350155