Stereocontrolled construction of octahydroquinolizines, octahydroindolizines, hexahydrobenzo[a]quinolizines, and an octahydroindolo[2,3-a]quinolizine by an intramolecular double Michael reaction: synthesis of (±)epilupinine
作者:Masataka Ihara、Tomoko Kirihara、Akihiro Kawaguchi、Mayumi Tsuruta、Keiichiro Fukumoto、Tetsuji Kametani
DOI:10.1039/p19870001719
日期:——
trifluoromethanesulphonate in the presence of triethylamine at –78 to 20 °C. A simple synthesis of an alkaloid, (±)-epilupinine, was accomplished. Hexahydrobenzo[a]-quinolizin-4-ones and an octahydroindolo[2,3-a]quinolizin-4-one were also constructed by the same method.
在两种不同条件下,从α,β-不饱和烯酰胺酯中立体控制一步合成八氢喹啉嗪和八氢吲哚嗪衍生物。在180-185°C下,在三甲基氯硅烷,三乙胺和氯化锌的存在下加热,在–78至20°C下,在三乙胺的存在下,用二甲基叔丁基甲硅烷基三氟甲磺酸酯处理。完成了生物碱(±)-癫痫素的简单合成。六氢苯并[一个]喹嗪-4-酮和八氢化吲哚并[2,3-一个〕喹嗪-4-酮也通过相同的方法构成。