Computer assisted organic synthesis/retrosynthetic analysis

Abstract

Retrosynthetic analysis is an essential tool for the design of multistep synthetic procedures. Sadly, even the more expensive chemistry drawing packages focus on molar retention and not on true retrosynthetic analysis and offer little, if anything, in terms of synthetic assistance. Most chemical drawing packages, such as ChemDraw (Regostered Trademark) or Chemsketch (Registered Trademark), allow for the generation of a SMILES code for any desired compound. A SMILES (Simplified Molecular Input Line Entry System) is a single line of text representing the connectivity of the molecule eg., acetic acid. The focus of this project was the development of a prototype program where SMILES codes could be used as both input (reactants) and output (products) for conducting synthetic and retrosynthetic methodologies. The resulting SMILES codes can easily be pasted into any chemical drawing package to view the resulting chemicals. Three simple, common organic reactions, SN2, esterification and Diels-Alder reactions, were investigated in the prototype program. We now wish to report on the initial success of this project. The program developed is capable of both synthetic and retrosynthetic reactions for SN2 and esterification reactions and synthetically for the Diels-Alder reactions. We will discuss the strategy required for constructing the program, its current limitations and its potential, if not as a research tool then as a teaching tool for undergraduate organic chemistry.