Computer assisted organic synthesis/retrosynthetic analysis

Tither, Darren and Marshall, Raymond L. (2005) Computer assisted organic synthesis/retrosynthetic analysis. In: Brisbane Biological and Organic Chemistry Symposium (BBOCS 2005), 25 Nov 2005, Brisbane, Australia.


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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 (Registered 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.

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Item Type: Conference or Workshop Item (Commonwealth Reporting Category E) (Paper)
Refereed: Yes
Item Status: Live Archive
Additional Information: Conference publication consists of only the abstracts of papers presented at the conference. Abstract only posted here.
Faculty/School / Institute/Centre: Historic - Faculty of Sciences - Department of Biological and Physical Sciences (Up to 30 Jun 2013)
Faculty/School / Institute/Centre: Historic - Faculty of Sciences - Department of Biological and Physical Sciences (Up to 30 Jun 2013)
Date Deposited: 11 Oct 2007 00:29
Last Modified: 18 Sep 2013 00:03
Uncontrolled Keywords: computer-assisted; organic synthesis; retrosynthetic analysis; chemical drawing packages
Fields of Research (2008): 06 Biological Sciences > 0601 Biochemistry and Cell Biology > 060113 Synthetic Biology
08 Information and Computing Sciences > 0803 Computer Software > 080301 Bioinformatics Software
03 Chemical Sciences > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis
Socio-Economic Objectives (2008): E Expanding Knowledge > 97 Expanding Knowledge > 970103 Expanding Knowledge in the Chemical Sciences

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