The Research On One-Pot Self-Organized Total Synthesis Of Natural Products And Their Analogues Based On Integration Of Organic Unit Reactions

Natural products are the most self-satisfied "design work" of nature.The existence of these active substances enables organisms to carry out life metabolism activities in an orderly manner.Their huge molecular library and natural affinity have obvious advantages in research and play an irreplaceable role in exploration and development of drugs.Therefore,the synthesis of natural products has attracted the attention of researchers.Under the guidance of the retro synthetic analysis proposed by Prof.E.J.Corey,most researchers have synthesized the target natural product molecules step by step.In the course of development,the synthesis trend of natural products has changed from the pursuit of synthesizing complex molecules to the study of simple,green and efficient synthesis of useful molecules.We believe that if we analyze and design the target molecule rationally and logically,finding a self-organizing synthetic route among many routes,which integrated unit reactions under the environment of a common chemical compatibility,bringing in the synthesis of natural products in one pot orderly,we can simplify synthesis steps and achieve self-organizing synthesis from artificial stepwise synthesis.In this paper,we chose natural evodiamine alkaloids,carbolines as the main research objects and achieved self-organizing synthesis of the target molecules in one pot.In addition,polysubstituted phenols were synthesized from enaminone,cinnamyl aldehyde and benzoyltrifluoroacetone respectively reacting with tricarbonyl compounds.This paper is mainly divided into the following parts:In chapter one,we summarized the background and significance of synthesizing natural products and introduced the advantages of one-pot self-organzing synthesis of natural products.Then we put forward the original intention and basis of this paper.In chapter two,based on the investigation of literatures,we have achieved the one-pot self-organizing synthesis of evodiamine and its analogues by using cheap substrate tryptamine,N-methyl isatoic anhydride and triethyl orthoformate after the design and analysis of the target product.In chapter three,the methods of synthesizing carboline alkaloids and their derivatives are reviewed.From the point of view of ideal synthesis,we synthesized?-carbolines from two kinds of amino acids in one pot.Combined with the literature investigation,we proposed the possible reaction mechanism through analyzing a series of control experiment.In chapter four,we classified the reported methods for the synthesis of polysubstituted phenols simply and described new ways of constructing polysubstituted phenol skeletons by formal cycloaddition reaction of tricarbonyl compounds with enaminone,cinnamyl aldehyde and benzoyltrifluoroacetone respectively.