Metal triflate-catalyzed cyclization of arylvinylcarbinols: formal synthesis of (±)-dichroanone and (±)-taiwaniaquinone H
作者:Badrinath N. Kakde、Subhadip De、Dhananjay Dey、Alakesh Bisai
DOI:10.1039/c3ra41497c
日期:——
A formal synthesis of diterpenoids viz. the taiwaniaquinoids (±)-dichroanone (1a) and (±)-taiwaniaquinone H (1b) possessing an all carbon quaternary stereocenter has been reported. The key step involves a metal triflate-catalyzed cyclization of arylvinylcarbinols, prepared from β-cyclocitral. The reaction possibly follows a stepwise mechanism via the intermediacy of arylallyl carbocationic species
正式合成二萜类化合物。据报道,具有全碳四元立体中心的台湾醌类(±)-二氢蒽酮(1a)和(±)-台湾醌H(1b)。关键步骤涉及由三氟甲磺酸酯催化的由β-环柠檬醛制得的芳基乙烯基甲醇的环化反应。该反应可能通过芳基烯丙基碳阳离子物质的中间体遵循逐步机理。