Carreño M. Carmen, García Ruano José L., Urbano Antonio
Departamento de Química Orgánica (C-I), Universidad Autónoma, Cantoblanco, 28049-Madrid, Spain.
J Org Chem. 1996 Sep 6;61(18):6136-6138. doi: 10.1021/jo960855n.
The synthesis of tetracyclic polyhydroxyquinones 5a and 5b was achieved through a sequence involving two Diels-Alder reactions with 1-methoxy-1,3-cyclohexadiene: the first with 2-(p-tolylthio)naphthazarin and the second on the resulting tricyclic derivative previously transformed into a (p-tolylsulfinyl)naphthazarin. The success of this strategy stemmed from the efficient remote regiocontrol exerted by the thioether substituent in the first step.
通过与1-甲氧基-1,3-环己二烯进行两步狄尔斯-阿尔德反应的序列实现了四环多羟基醌5a和5b的合成：第一步是与2-(对甲苯硫基)萘并azarin反应，第二步是在先前转化为(对甲苯亚磺酰基)萘并azarin的所得三环衍生物上进行反应。该策略的成功源于第一步中硫醚取代基施加的有效远程区域控制。
