Synthetic Studies Toward Artemisinin And Michellene G

In this thesis,the synthesis of artemisinin and michelene G by MHAT reaction as a key step was explored.This thesis is divided into three parts.In the first chapter,firstly,the application of MHAT reaction in the total synthesis of natural products is summarized.We designed the MHAT reaction of terminal unactivated monosubstituted olefins to construct 6/6 ring and the reaction was studied.Eventually,we successfully constructed a 6/6 ring through the tandem Double Michael method promoted by MHAT,but the yield and selectivity of the MHAT reaction need to be further explored and improved.In the second chapter,the important role of artemisinin in malaria treatment and the shortage of artemisinin in the world were introduced.Then it summarized the total synthesis of artemisinin,the bionic synthesis of artemisinin and the industrial production of artemisinin.After that,we successfully constructed 6/6 ring using MHAT reaction as the key step,constructed tricyclic skeleton through reduction endo esterification reaction,then constructed key intermediate through ring opening reaction,and finally studied the synthesis of artemisinin.In the third chapter,the new tetracyclic sesquiterpene lactones Mitchellenes a-c,and other mitchellenes compounds isolated by Davis research group from the Australian plant Eremophila mitchellii were introduced.In 2018,the Greatrex research group proved that the compounds of Mitchellenes came from the plant E.sturtii and isolated two new compounds of Mitchellenes F and G.The biomimetic synthesis of compounds from Mitchellenes was outlined thereafter.We have successfully constructed the 6/6 ring and chiral center in Mitchellene G via MHAT reaction,which will provide new strategy for the synthesis of this family of the molecules.