Studys On The Total Synthesis Of A Novel Naphthalene Lignan

Naphthalene lignans are an important component of lignan compounds,and the number of natural products is relatively high.Naphthalene lignans have a wide range of biological activities,such as anti-tumor,anti-oxidation,anti-inflammatory,liver protection,immunosuppressive activities,etc.,and can be used as alternative drug molecules,which have good medicinal value.After research,it was found that Olenaisoindole A,a natural product of naphthalene lignans,has a good inhibitory effect on breast tumor cells and leukocytes,and also has a good anticholinase effect.This project decided to conduct a total synthesis study on the natural product of naphthalene lignans Oleraisoindole A.The specific content can be divided into the following sections:The first part is the introduction.First,I summarized the origin,definition,classification,physicochemical properties,biological activity,extraction and separation,synthesis research progress,and topic background of lignan compounds,and conducted the latest research on naphthalene lignan to sum up.Based on previous research experience and structural analysis of the target compound Oleraisoindole A,a route for the synthesis of Oleraisoindole A was designed.The second part is the experimental part.First,based on the reverse synthesis analysis of the natural product Oleraisoindole A,the total synthetic work was carried out according to the experimentally designed synthetic route.Vanillin and tyramine are the best starting materials for the synthesis of naphthalene lignan Oleraisoindole A.Tyramine is obtained through a three-step reaction to obtain a tyramine intermediate,including amino protection reaction,phenol hydroxyl protection reaction and amino reduction reaction;Vanillin has a phenolic hydroxyl protection reaction,two Stobbe condensation reactions,ethanol esterification reaction,dimethyl sulfate methylation reaction,and electrocyclization oxidation reaction to obtain the naphthalene lignan skeleton structure,followed by hydrolysis reaction and dehydration.The natural product Oleraisoindole A was obtained by reaction,acylation reaction and Pd/C catalytic hydrogenation reaction.The third part is the result discussion and analysis.This part mainly discusses and analyzes the reaction conditions,reaction mechanism,and possible negative reactions in the synthetic route,which is convenient to optimize the optimal reaction conditions.This section also includes the preparation of some special reagents used in the reaction and experimental precautions.In order to maximize the synthesis yield of Oleraisoindole A,accurate analysis was performed.