Electrochemical synthesis of chroman and euglobal skeletons via cycloaddition reaction of o-quinone methides and alkenes
作者:Kazuhiro Chiba、Junko Sonoyama、Masahiro Tada
DOI:10.1039/p19960001435
日期:——
synthesized by the intermolecular cycloaddition reaction of terpenes and o-quinone methides generated in situ by electrochemical oxidation. In a two-phase reaction medium composed of hexane-lithium perchlorate/nitromethane, 2-[1-(propylsulfanyl)alkyl]phenols were selectively oxidized to give the corresponding unstable o-quinone methides. These intermediates were trapped in situ by unactivated alkenes or easily
通过萜烯与通过电化学氧化原位生成的邻醌甲基化物的分子间环加成反应合成了Euglobal骨架。在由己烷-高氯酸锂/硝基甲烷组成的两相反应介质中,将2- [1-(丙基硫烷基)烷基]酚选择性氧化,得到相应的不稳定的邻醌甲基化物。这些中间体被未活化的烯烃或易氧化的萜烯原位捕获,形成各种色度和螺色度,包括真球形。特别是,在β蒎烯的存在下,蓝桉醛II b骨架,其具有一个β水芹烯基部分,通过环加成形成经由 β-pine烯的骨架重排。