Synthetic Studies Of Ferrocene Derivates And The Skeleton Of (+)-9(11)-Dehydroestrone Methyl Ether

This thesis mainly focused on two parts: The sythesis of ferrocene derivates and the total synthesis towards the skeleton of (+)-9(11)-dehydroestrone methyl ether. In addition, one-pot enzymatic resolution in ionic liquid was also investigated.In the first part, we utilized the techniques of solvent-free condition and ultrasonic irradiation to design and synthesis a series of ferrocenyl substitutedα,β-unsaturated ketones and pyridine derivatives. It was found that the reactions under solvent-free condition or ultrasonic irradiation could be conducted simply under milder condition in a shorter reaction time and obtained higher yields, comparing with conventional methods.In the second part, we synthesized the skeleton of (+)-9(11)-dehydroestrone methyl ether. It was found that Indium tribromide could efficiently catalyze the Mukaiyama-Michael addition of silyl enol ether to 2-methyl-2-cyclopenten-1-one under neat condition, then the diketone product was subjected with allyl bromide under thermodynamic control giving the important intermediate of the whole procedure. Then subsequent transformations lead to the final target molecular successfully.Meanwhile, some substrates were gave the acylated products in good yields and enantioselectivity (45-96% e.e.) in one-pot enzymatic resolution in ionic liquid.