Computer assisted organic synthesis/retrosynthetic analysis

Paper


Tither, Darren and Marshall, Raymond L.. 2005. "Computer assisted organic synthesis/retrosynthetic analysis." Arnold, Dennis and Atefi, Farzad (ed.) Brisbane Biological and Organic Chemistry Symposium (BBOCS 2005). Brisbane, Australia 25 Nov 2005 Brisbane, Queensland.
Paper/Presentation Title

Computer assisted organic synthesis/retrosynthetic analysis

Presentation TypePaper
AuthorsTither, Darren (Author) and Marshall, Raymond L. (Author)
EditorsArnold, Dennis and Atefi, Farzad
Journal or Proceedings TitleBrisbane Biological and Organic Chemistry Symposium 2005
Number of Pages1
Year2005
Place of PublicationBrisbane, Queensland
ISBN9781876731076
Conference/EventBrisbane Biological and Organic Chemistry Symposium (BBOCS 2005)
Event Details
Brisbane Biological and Organic Chemistry Symposium (BBOCS 2005)
Event Date
25 Nov 2005
Event Location
Brisbane, Australia
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 (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.

Keywordscomputer-assisted; organic synthesis; retrosynthetic analysis; chemical drawing packages
ANZSRC Field of Research 2020310113. Synthetic biology
460103. Applications in life sciences
340503. Organic chemical synthesis
Public Notes

Conference publication consists of only the abstracts of papers presented at the conference. Abstract only posted here.

Byline AffiliationsLearning & Teaching Support
Department of Biological and Physical Sciences
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https://research.usq.edu.au/item/9xqv2/computer-assisted-organic-synthesis-retrosynthetic-analysis

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