Introduction to Organic Synthesis Lectures last modified Chemistry：在有机合成化学的介绍讲座最后修改.docVIP

Introduction to Organic Synthesis CM3001 Dr. Alan Ford (Lab 415) text: Willis Wills Organic Synthesis (OUP) To state the obvious: Synthesis is the process of making a desired compound using chemical reactions. More often than not, more than one step is involved. The importance of synthesis Total synthesis of interesting and/or useful natural products Industrially important compounds compounds of theoretical interest structure proof development of new synthetic methodology importance to other areas of science and technology Examples Natural products eg. steroids, prostaglandins, alkaloids15-Methyl PGF2α (prostaglandin) Epibatidine (South American frog alkaloid) 15 mg isolated from 750 frogs Industrially important compounds such as pharmaceuticals, agrochemicals, flavours, dyes, cosmetics, monomers and polymers Naproxen (painkiller) Carbaryl (insecticide) Sarin (nerve gas) Isobutavan Methylenedioxymethamphetamine, MDMA(smells of mint chocolate) (Ecstasy) 5 CB (liquid crystal) Kevlar (fancy polymer) Theoretically interesting molecules  Cubane meta para Cyclophane Structure proof While spectroscopy and crystallography are used to determine molecular structures, unambiguous total synthesis is still important S-(+)-Chelonin B (marine sponge alkaloid) New methodology New ways to make molecules, improvement of existing ways, ways of doing what was previously impossible Science and Technology Materials with special applications; molecular switches, non-linear optics, nanotechnology Basic Steps of Solving Synthetic Problems 1) Choice of TARGET MOLECULE (TM) 2) Consideration of applicable synthetic methodology 3) Design of synthetic pathway 4) Execution of the synthesis —these steps are highly interactive Approaching the design of a synthesis (Part One) For simple molecules it can be obvious just by looking at the target structure, for example: Cyclohexyl bromide Bromoalkanes are available from alkenes or from alcohols Methyl benzoate Esters ar