Studies On The Synthesis Of Athrotaxin

Cyclohexadiene ketone is a very important, multiple functionalized synthetic block, wh-ich could be obtained by oxidative dearomatization from aromatic derivatives. Oxidative dearomatization reaction is widely used in the natural producs synthesis. In this thesis, we repoted the synthesis of Athrotaxin, a lignan category natural product by mainly HWE, M-ichael addition and oxidative dearomatization reactions.This thesis is divided into four chapters. The first chapter mainly introduces the Horn-er-Wadsworth-Emmons reaction research progress and its application in organic synthesis. The common agents for the oxidative dearomatization reaction, and some examples in the natural product synthesis with HWE reaction were summarized.The second chapter introduces the strategy of using oxidative dearomatization reaction to synthesize Athrotaxin. In the first, we attempted to use D-mannitol as the chiral pool in the following Horner-Wadsworth-Emmons reaction to control the configuration of the main intermediate for the synthesize Athrotaxin. Since the first route was not success, we reported detail construction of basic framework of Athrotaxin by achiral synthesis. In this chapter, we also reported the encountered problems and solutions in the synthetic studies.In third chaper, the synthesis studies by both asymmetric and racemic routes in this t-hesis were summarized and future work proposed.In fourth chapter, the detail of experiment operation and the spectrographic data of all the compounds synthesized in the thesis were reported.The structures of products and intermediates in this thesis were confirmed through the NMR instrument’s analysis.