【摘要】 本文报道(±)-表-马氏醇(epi-mayol)(1)的全合成,将8-羟基香叶醛(4)与溴代苯硫醚(5)在Cr(Ⅱ)作用下立体选择地缩合生成苏式—(2E,8E,12E)—3,9,13—三甲基—6—异丙烯基—2,8,12-十四碳三烯-7,14-二羟基苯硫醚(6).6转变为对甲苯磺酸酯后,在LDA作用下闭环得环化产物(2E、6E、10E)-1-羟基-3,7,11-三甲基-9-苯硫基-14-异丙基-2,6,10-十四碳环三烯(9).9脱去苯硫基得目标化合物1.更多还原

【Abstract】 The tatol synthesis of (±)-epi-mayol (1) using a readily available geraniol as starting material is described. The stereospecific coupling of the two substituted geranyl units was achieved by the reaction of 8-hydroxy-geranial (4) with 8-bromo-geranyl-phenyl-thioether (5) in the presence of Cr(Ⅱ) reagent. The resultant mixture was purified with flash chromatography on SiO2 to give compound 6 and its diastereoisomer 7 in 56% and 7% yield respectively. 6 was converted to tosyl ester 8 and followed by ring closure in the presence of LDA gave compound 9. The pheny-thio group in 9 was cleaved by sodium-t-butanol to give the title compound (±)-epi-mayol (1).更多还原