Studies Towards The Synthesis Of Athrotaxin

Cyclohexadienones produced by oxidative dearomatization are important and multifunctional building blocks,which have been used as intermediates for the synthesis of natural product and its analogues.Many synthetic efforts have been devoted to this field in recent years.This thesis describes a new approach towards the synthesis of Athrotaxin using the oxidative dearomatization strategy.This thesis is composed of three chapters.In the first chapter, recent progress of oxidative dearomatization reactions and its applications in the synthesis of natural product synthesis is summarized. A number of common synthetic methods for oxidative dearomatization are presented. Synthesis of natural products based on oxidative dearomatization strategy is also presented in this chapter.In the second chapter, synthetic studies on Athrotaxin using a oxidative dearomatization strategy is discussed in detail. Athrotaxin is a lignan isolated from the heartwood of the Taxsmanian conifer Athrotaxis selaginoides with an unique spiro hexadienone structure. We designed a new synthetic route towards the synthesis of Athrotaxin starting from o-methoxy phenol. The athrotaxin skeleton was constructed in 9 steps. Asymmetric synthesis of athrotaxin was also discussed in this chapter.In the third chapter,experimental data and procedures for all compounds is presented.