Design And Synthesis Of 2,5-diketopiperazine Derivatives

Natural products with the skeleton of 2,5-diketopiperazine are widely distributed in plants,animals even fermentation products.According to the recent research,it was found that 2,5-diketopiperazines(2,5-DKPs)usually showed bioactivity of anti-tumor and anti-viruses.The traditional strategies to build the skeleton of 2,5-DKPs via condensation reactions of two amino acids suffer from the disadvantages of low yield,complex conditions and high costs.Those negative impacts have limited further research for 2,5-diketopiperazine containing compounds.In this thesis,we focus on developing a new method for the synthesis of 2,5-DKPs.We design and synthesize several 2,5-DKPs from some common and inexpensive amino acids via our method.The method has the advantages of high yield,simple reaction condition,wide range of substrate,and can be used in gram scale synthesis.Three chapters are included in this thesis:In the first chapter,phytochemistry and bioactivity of 2,5-DKPs were summarized.The strategies of the synthesis used for 2,5-DKPs were also described.In chapter two,the synthesis of 2,5-DKPs was described.After the synthesis of the key alkyne intermediates,the skeleton of 2,5-Diketopiperazine were afforded by the intramolecular coupling of amide with alkynes using triphenylphosphine as catalyst.In chapter three,the detailed experimental procedure and spectrum data for related compounds and intermediates described in chapter 2 are recorded.