Asymmetric Norrish/Yang Photo Reaction Of 6-Carbonyl Substituted Bicyclo [3.1.0] Hexane

The new asymmetric synthesis using solid-phase photochemical reactions isdeveloped by professor Scheffer group. This approach not only applies characters andadvantages of photochemical reaction and solid phase reaction, but more importantly, is anew idea in the field of asymmetric synthesis and have a very broad application andresearch value. This approach has raised great interest and concern among the chemists.The main research contents of this paper has two aspects, we use [2.2.1] heptadieneas the starting material, after oxidation of peracetic acid and silver nitrate, diazomethaneesterification, lithium aluminum hydride reduction, tert-butyl dimethyl chlorosilaneprotection borohydride oxidation, acetyl protection, remove TBS protection, oxidation ofalcohol to aldehydes using swern oxidation, to form reaction step synthesis ofintermediate 6-carbonyl substituted bicyclo[3.1.0]hexane derivatives, After photoreaction,cyclopentene derivatives with two chiral centers is abtained through intramolecularNorrish / Yang reaction, the target product can be used to synthesize prostaglandin-typedrugs; we try to change the experimental conditions and different reagents and increasethe yield.Cyclopentene derivatives are very important intermediates to synthesizeprostaglandins and its derivatives. Therefore, this thesis is very useful for the synthesis ofthe drug and helpful to the application of photochemical reactions to the synthesis ofchiral drugs. We successfully synthesized cyclopentene derivatives. Experimentalmethods is with mild conditions, rapid reaction, high yield, and such compounds inorganic synthesis and applications have great prospects.