synthesis of the key intermediate of coenzyme q10关键中间体的合成辅酶q10.pdfVIP

Molecules 2011, 16, 4097-4103; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of the Key Intermediate of Coenzyme Q10 Fan-Song Mu 1,2,†, Meng Luo 1,2,†,*, Yu-Jie Fu 1,2, Xuan Zhang 1,2, Ping Yu 1,2 and Yuan-Gang Zu 1,2,* 1 Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, China; E-Mails: fansong2006@126.com (F.-S.M.); fuyujie1967@ (Y.-J.F.); 350330842@163.com (X.Z.); yup2010@163.com (P.Y.) 2 Engineering Research Center of Forestry Bio-preparation, Ministry of Education, Northeast Forestry University, Harbin 150040, China † These authors contributed equally to this work. * Authors to whom correspondence should be addressed; E-Mails: wslm_5555@ (M.L.); zygorl@ (Y.-G.Z.); Tel.: +86-451-8219-0535; Fax: +86-451-8219-0535. Received: 24 March 2011; in revised form: 9 May 2011 / Accepted: 9 May 2011 / Published: 18 May 2011 Abstract: (2’E)-1-(3-methyl-4-p -toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene (4) is the key intermediate in the synthesis of coenzyme Q10 via a coupling reaction with solanesyl bromide. In this paper, we report a simple and effective synthesis of compound 4, starting with the readily available and inexpensive precursors p -toluenesulfonyl chloride (TsCl) and isoprene to obtain (2E)-1-p -toluenesulfonyl-2-methyl-4-hydroxy-2-butene (3) by addition, esterification and hydrolysis. Application of the Friedel-Crafts alkylation