Design And Synthesis Of Sterol Compounds And Research On The Synthesis Of Aglycone Skeleton Of Phyllanthusol Compounds

Oxysterol are widely found in nature and a lot of them exhibit various biological activities.Oxosterol were obtained by multi-step reactions from cholesterol compounds.Oxidation reactions can occur on the sterol core or side chain.In recent years,it has been found that the introduction of nitrogen heteroatoms on steroidal nuclei or the introduction of nitrogen-containing functional groups in steroidal branches make the produced steroids show good pharmacological activities.Nitrosterol is an electronic equivalent of Oxysterol.In the first part of this thesis,23 compounds(16 of which are new compounds that have never been reported)have been synthesized.The studies of their antitumor activity are now under investgation and it is hoped that the results will be useful for the future researches of this kind compounds.Myrrh is a common traditional Chinese medicine.It is a dry resin from the myrrh plant of the olive plant.In recent years,some researchers have discovered that natural myrrh compounds have good antitumor activities.Moreover,the structures of the high oxidized myrrh are complex and have similar structures with spiro ketal.The Phyllanthusol compounds extracted from the Phyllanthus acidus Skeel were represence of such compounds.In the second part of this thesis,we have been discussed the synthesis of aglycone part of Phyllanthusol B.In our beginning synthesis,2-phenyl-1,3-dioxan-5-one(2-41)was obtained from trihydroxymethyl aminomethane hydrochloride as raw material,with Trimethyl phosphonoacetate through HWE and Baylis-Hillman reaction and substitution reaction obtained methyl 2-(bromomethyl)acrylate(2-35),according to Casey's method,we get methyl(1S,3S)-9-oxo-3-phenyl-2,4-dioxabicyclo[3.3.1]nonane-7-carboxylate(2-50).Compound 2-50 and compound 2-55 get compound 2-57 through HWE reaction.The further modification included removal PMB protection from compound 2-57 followed with intramolecular cyclization reactions.However,we did not obtain the desire PMB deprotection product,instead,the hydroxyl dehydration product was always formed even we try a series of different conditions.Due to the time,we did not finish the synthesis of the final target molecular,but the whole skeleton was built.All the structures of compounds reported in the synthesis were characterized by 1H-NMR and 13C-NMR spectrometer.