Studies On The Total Synthesis Of Neolignans And Stilbene Compounds

This thesis main focused on the syntheses of a few naturally occurring 8-O-4' neolignans, coumarin-stilbene, two resveratrol derivatives, and two novel sesquineolignans. Its included the following four parts:Chapter 1. The progress on the constructing of substituted tetrahydropyran during twenty years (review)The review introduced some methods on the building of substituted tetrahydropyran, and which were applied in the synthesis of natural products.Chapter 2. Asymmetric total synthesis of several naturally occurring 8-0-4' neolignas and its' enantiomerThe definition, previous synthetic reports of 8-O-4' neolignas were introduced in brief. All the enantiomer of 8-O-4' neolignans Virologins E, F, and G were first synthesized starting from 4-hydroxy-3,5-dimethoxybenzaldehyde and 1-(3,4,5-trimethoxyphenyl)-propan-2-ol, using Mitsunobu reaction as key step.Chapter 3. First total synthesis of two resveratrol derivatives and a novel stilbene-coumarin.The activity of resveratrol and coumarin were introduced in brief. Two resveratrol derivatives and a novel stilbene-coumarim were first synthesized starting from the derivative of 3,5-dihydroxybenzoic acid, using Horner-Emmons reaction to construct the stilbene and Baker-Venkataraman rearrangement to build the 4-hydroxycoumarin as key steps. Meanwhile, the anti-tumour activity and the structure of the three natural compound and some intermediate also were studied.Chapter 4. Study on the enantioselective total synthesis of two novel sesquineolignans which bears a 2,3,5-trisubstituted tetrahydropyran Morinols A and BThe definition, classification of lignans were introduced briefly. The approach of enantioselective total synthesis of Morinols A and B was studied starting from dihydrofuran-2(3H)-one. In which Aldol reaction and Baylis-Hillman reaction was key steps.This thesis concerned the asymmetric total synthesis of 8-0-4' neolignans, the total synthesis of two resveratrol derivatives and a novel stilbene-coumarin, studied the enantioselective synthesis of two sesquineolignans with a new skeleton which include a 2,3,5-trisubstituted tetrahydropyran. The structures of the compounds were identified by spectral analysis methods.