Studies On The Synthesis Of Solasodine And [2+4] Cycloaddition To Construct Isoquinoline Ring

Solasodine is a steroidal alkaloid from the nightshade plant and can be combined with different kinds of glycosides and varying amounts of glycosides to form a variety of glycoalkaloids.These alkaloids have a variety of pharmacological activities which can exert anti-oxidation,nutrient-producing nerve cells,fungi inhibition,etc..Especially they have strong pharmacological effects on antitumors.In addition,some of the inorganic and organic solanine acid salts also have good pharmacological activities,and have extensive applications in anti-cancer and anti-asthma.Therefore,this class of compounds has attracted much attention in related fields,and more research work has been done on the total synthesis of such complex natural product molecules.Based on the interests in activities and structures of these natural products,we chose solasodine as the research target,and designed two different synthetic routes for it.We synthesize Solasodine according to the synthetic route II by analyze the experimental results.And through the process of hydroxy esterification,ring opening,oxidation and reductive amination,the precursor compounds of solasodine were obtained.Isoquinoline alkaloids are based on isoquinoline skeletons and are widely found in various types of products.They have a wide variety of structures and diverse biological activities.For a long time,due to its wide application in the field of medicine,researchers have invested a lot of energy in constructing isoquinoline skeletons.At the same time the classical three methods for the construction of isoquinoline rings are Bischler-Napieralski reaction,Pomeranz-Fritsch reaction and Pictet-Spengler reaction,In recent years,owing to the high performance of transition metals in oxidative coupling reactions,researchers have success in the construction of isoquinoline rings through the transition metal-catalyzed oxidative coupling reactions,and have made considerable progress.Based on related reviews of isoquinoline ring construction and transition metal-catalyzed oxidative coupling,We proposed the [2+4] cycloaddition reations to build isoquinoline rings by reacting oxadiazolone-directed group and quinoline-directed group aryl compounds with diazo compounds,or other substates such as halogenated olefins,arylhalides,on the condition of transition metals catalysis.