Synthesis And Study Of New Aspartyl Protease Inhibitor YF-0200R-A And B

This thesis introduced the total synthesis of two natural unsaturated fatty acids with aspargyl protease inhibition activity. The relative configuration and the absolute configuration were confirmed. Both of these natural compounds were firstly separated from southern Sumatra soil samples. The planar structures were studied by nuclear magnetic resonance(NMR), mass spectrometry and other instrument analysis methods, but the relative configuration and absolute configuration were not determined.In this paper, two parts were written to introduce the processes of total preparation of four compounds.The process of preparing(2E,4E,8R,10R) and(2E,4E,8S,10R)-8,10,12-trihydroxydodeca-2,4-dienoic acid was introduced in the first part. D-glucose was used as rare material to install epoxy chiral building blocks. The final production was synthesized by radical mediated deoxygenation, Horner-Wadsworth-Emmons reaction and other reactions. The absolute configurations for natural YF-0200 R B could be reliably assigned as(8S,10S) by analyzing the spectroscopic data, 1H NMR and 13 C NMR.In the second part,(8R,2E,4E) and(8S,2E,4E)-8,12-dihydroxydodeca-2,4-dienoic acid were totally synthesized. During the process, asymmetric allylation, hydroboration, oxidation and Horner-Wadsworth-Emmons reaction were used to prepare the optically active target compounds with(8R) and(8S) configurations, respectively. Assignments of the absolute configurations,(8S), of YF-0200 R A were made on the basis of comparison of the 1H and 13 C NMR as well as optical rotations.