【摘要】 癸异戊二烯醇 (Ⅵ )是极具药用价值药物辅酶Q10 (Ⅶ )的侧链。利用茄尼醇 (Ⅰ )为原料 ,与PBr3 在无水乙醚中反应得到茄尼基溴 (Ⅱ ) (产率 90 % ) ,Ⅱ溶于无水DMF与无水PhSO2 Na反应得到茄尼基砜 (Ⅲ ) (产率 92 % ) ,Ⅲ在叔丁醇钠催化下 (此方法未见报道 )或在相转移催化下与 (E) 3 甲基 4 溴 2 丁烯 1 醇乙酸酯 (Ⅳ )反应偶联得到 (E ,E ,E ,E ,E ,E ,E ,E ,E ,E) 3,7,11,15 ,19,2 3,2 7,31,35 ,39 十甲基 5 苯磺酰基 2 ,6 ,10 ,14,18,2 2 ,2 6 ,30 ,34 ,38 四十碳十烯 1 醇 (Ⅴ ) (产率分别为 89%、19% ) ,将Ⅴ溶于无水甲醇中 ,用Na/Hg齐还原去砜基得到癸异戊二烯醇 (产率6 7% )。用IR、1HNMR、MS验证化合物的结构 ,与文献报道一致。更多还原

【Abstract】 Decaprenol (Ⅵ),the side chain of coenzyme Q 10 (Ⅶ),is synthesized from the starting material solanesol(Ⅰ).Bromination of (Ⅰ) by PBr\-3 produced solanesyl bromide (Ⅱ) in 90% yield,which reacts with PhSO\-2Na in anhydrous DMF to get solanesyl sulphone (Ⅲ) in 92% yield.(E,E,E,E,E,E,E,E,E,E) 3,7,11,15,19,23,27,31,35,39 decamethyl 5 phenylsulfonyl 2,6,10,14,18,22,26,30,34,38 tetracontadecaen 1 ol (Ⅴ) is prepared by the coupling of Ⅲ and (E) 4 bromo 3 methyl 2 butenyl acetate (Ⅳ),catalyzed by sodium t butoxide (89% yield) or phase transfer agent TBAB (19% yield).Ⅵ is obtained by the reductive elimination of the phenylsulfonyl group of Ⅴ in 67% yield.The structure of Ⅵ is confirmed by IR,NMR and MS.更多还原