Construction Of Tetrahydrocannabinol Skeletons And Study On Total Synthesis Of Sanjoseolide

This thesis aimed at the studies on the construction of tetrahydrocannabinol skeletons and the total synthesis of sanjoseolide,the detail contents could be divided into the following two parts:Chapter 1.Studies on the Construction of Tetrahydrocannabinol skeletons.Tetrahydrocannabinol is a kind of tricyclic and bichiral cannabinoid isolated from genus Cannabis(Moraceae)in plant Cannabis Sativa L.These compounds have a good inhibitory effect on the central nervous system(CNS)and the tractus solitaries nucleas(NTS)and have been shown to be effective for acesodyne,sedative,resistance,anti-nausea,antiglaucoma and antihypertension.Firstly,by analyzing the structures of these compounds,we considered that tricyclic cannabinoid with fundamental skeleton could be obtained through catalytic asymmetric hydrogenation,the subsequent functional groups transformation and intramolecular regioselective dehydration,?~9-Tetrahydrocannabinol and?~8-Tetrahydrocannabinol were obtained respectively.Later,we tried to synthesize the tetrahydrocannabinol by using olivitol as initial agents via Friede-Crafts acylation and Domino Michael-Aldol reaction workup directly delivers?~9-Tetrahydrocannabinol(?~9-THC)in 24.6%and?~8-Tetrahydrocannabinol(?~8-THC)29.6%overall yields over seven steps.Chapter 2.Study on the Total Synthesis of Sanjoseolide.Sanjoseolide is a kind of isoprenylated chalcone isolated from Dalea frutescens,which contains an unique hydroxyisoprenyl group,these compounds have slightly greater cytotoxic activities and anti-proliferative activities against tumor cells.Firstly,by analyzing the structures of sanjoseolide,the step one is to introduce the side chain of isopentenyl,the step two is to change the side chain into dihydroxy isopentenyl,the step three is to synthesis the skeleton of chalcone.Introducing the side chain by alkylation of phenolic hydroxyl group and Claisen rearrangement reaction;Modifying side chain groups through epoxidation and asymmetric dihydroxylation;chalcone skeleton could be obtained through Aldol reaction,Sanjoseolide was obtained.Then we tried to synthesize the sanjoseolide by using 2,4-dihydroxyacetophenone as initial agents via Claisen rearrangement reaction and Aldol reaction etc.Obtaining the sanjoseolide plan over nine steps.