Synthesis Of The Natural Product Homofascaplysin And Analogues By Photocyclization Reactions

Organic photochemical reaction has become an important way for synthesis of natural products. This thesis mainly deals with on synthesis of homofascaplysin B, B-1, C and analogues by the photocyclization of3-acyl-2-chloro-l-[2-(indol-3-yl)ethyl]indoles. It consists of two parts:The first part of this thesis is a literature review, including briefly introduction of organic photochemical dehalogenation reaction mechanism and modern photochemical dehalogenation reaction, and the research of reactions of halogenated aromatics and halogenated heteroaromatics with aromatics, alkenes, alkynes and so on.The second part is the introduction of my research work. The synthesis of homofascaplysin B, B-1, C and analogues has been finished through two routes. The first was via one-pot Cu(OAc)2-catalyzed dechlorination cyclization and oxidation dehydrogenation; the second was via photoinduced dechlorination cyclization and DDQ oxidation dehydrogenation. A new and efficient synthetic homofascaplysin has been established.