The friedel-crafts allylation of a prenyl group stabilized by a sulfone moiety: expeditious syntheses of ubiquinones and menaquinones

JH Min, JS Lee, JD Yang, S Koo

Index: Min, Jae-Hong; Lee, Jun-Sup; Yang, Jae-Deuk; Koo, Sangho Journal of Organic Chemistry, 2003 , vol. 68, # 20 p. 7925 - 7927

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Citation Number: 44

Abstract

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 ...