Synthesis And Determination Of Absolute Configurations Of Six Natural Phenylpropanoids

Phenylpropanoids are a kind of natural products, which widely exists in plants,have important applications in many fields such as medicine, food, cosmetics. Manycompounds have a variety of biological activity, therefore, showing a goodapplication prospect in medicine, biology and other fields. As early as the late1950s,study found that aralia plants have the ginseng-like effects, and get attention ofpeople. Several natural products of this article to synthesis are the latestphenylpropanoid compounds separated from plants aralia, it has not been reported inthe synthesis, so far.This thesis is started with p-hydroxy benzaldehyde, after nucleophilicsubstitution, ester hydrolysis, prosthetic group protection, Wittig reaction, selectivemethylation, auxiliary removal reduction reaction as well as oxidation, reductionreactions to complete the total synthesis of natural phenylpropanoids （R）-2-1,（S）-2-2,（S）-2-3,（R）-2-4,（S）-2-5,（S）-2-6; Using chiral auxiliary of opposite configuration tobuild chiral center, obtained the natural products enantiomers （S）-2-1,（R）-2-2,（R）-2-3,（S）-2-4,（R）-2-5; Determined the absolute configuration of natural products2-1and2-4is R-type, natural products2-2,2-3,2-5and2-6is S-type.Natural products2-1,2-2,2-3,2-4and2-5and enantionmers finally areconfirmed fully consistent with the literature by¹H NMR,¹³C NMR, IR, MS andother spectral data.In this paper, the configuration of the synthetic compound2-6（88%ee） isS-type, the same as the rotation direction of the literature, there is a big difference invalue.In this article,20intermediates synthesized are new compounds that have notbeen reported, and are given structure characterization by¹H NMR,¹³C NMR, IR, MS and other detection methods.