Abstract
In this paper, we present an application of case-based reasoning to the design of synthetic plans in organic synthesis. First, we briefly introduce the principles of organic synthesis planning, e.g. building a new molecular structure or target molecule. Then, we present the knowledge representation and reasoning principles on which relies the system for organic synthesis planning that we are developing. Two main kinds of reasoning processes are employed in the system. Classificationbased reasoning is used at a tactical level for the perception of chemical characteristics and the structure modifications of the target molecule. Case-based reasoning is used at a strategic level to build a synthetic plan, according to the similarity between the target molecule and memorized synthetic plans. The representation and the handling of one-step synthetic plans are detailed and end the paper.
This is a preview of subscription content, log in via an institution.
Preview
Unable to display preview. Download preview PDF.
References
H. Bunke and B.T. Messmer. Similarity Measures for Structured Representations. In M.M. Richter, S. Wess, K.-D. Althoff, and F. Maurer, editors, Proceedings of the First European Workshop on Case-Based Reasoning (EWCBR'93), Kaiserslautern, pages 26–31, 1993.
J.G. Carbonell. Derivational Analogy: A Theory of Reconstructive Problem Solving and Expertise Acquisition. In R.S. Michalski, J.G. Carbonell, and T.M. Mitchell, editors, Machine Learning, an Artificial Intelligence Approach, Volume II, pages 371–392. Morgan Kaufmann Publishers, Inc., Los Altos, California, 1986.
E.J. Corey and X.M. Cheng. The Logic of Chemical Synthesis. John Wiley & Sons, New York, 1989.
E.J. Corey, A.K. Long, and S.D. Rubenstein. Computer-Assisted Analysis in Organic Synthesis. Science, 228:408–418, 1985.
P.T. Devanbu and D.J. Litman. Plan-based Terminological Reasoning. In Proceedings of the Second International Conference on Principles of Knowledge Representation and Reasoning (KR'91), Cambridge, Massachusetts, pages 128–138, 1991.
J. Lieber. Étude du raisonnement par cas. Rapport de Recherche 93-R-043, Centre de Recherche en Informatique de Nancy, 1993.
G. Masini, A. Napoli, D. Colnet, D. Léonard, and K. Tombre. Object-Oriented Languages. Academic Press, London, 1991.
J. Mostow. Design by Derivational Analogy: Issues in the Automated Replay of Design Plans. Artificial Intelligence, 40:119–184, 1989.
A. Napoli. Using Frame-Based Representation Languages to Describe Chemical Objects. New Journal of Chemistry, 14(12):913–919, 1990.
A. Napoli. Subsumption and Classification-Based Reasoning in Object-Based Representations. In Proceedings of the 10th European Conference on Artificial Intelligence (ECAI'92), Vienna, Austria, pages 425–429, 1992.
B. Nebel. Reasoning and Revision in Hybrid Representation Systems. Lecture Notes in Computer Science 422. Springer-Verlag, Berlin, 1990.
T. Okada and T. Kawai. Analogical Reasoning in Chemistry (1. Introduction and General Strategy, 2. DNET/MS System). Tetrahedron Computer Methodology, 2(6):327–347, 1989.
M.M. Richter. Classification and Learning of Similarity Measures. In Opitz, Lausen, and Klar, editors, Studies in Classification, Data Analysis and Knowledge Organization. Springer-Verlag, Berlin, 1992.
L.G. Shapiro and R.M. Haralick. Structural Descriptions and Inexact Matching. IEEE Transactions on Pattern Analysis and Machine Intelligence, 3:504–519, 1981.
I. Ugi, M. Wochner, E. Fontain, J. Bauer, B. Gruber, and R. Karl. Chemical Similarity, Chemical Distance, and Computer-Assisted Formalized Reasoning by Analogy. In M.A. Johnson and G.M. Maggiora, editors, Concepts and Applications of Molecular Similarity, pages 239–288. John Wiley & Sons Ltd, Chichester, West Sussex, 1990.
M.M. Veloso and J.G. Carbonell. Derivational Analogy in Prodigy: Automating Case Acquisition, Storage, and Utilization. Machine Learning, 10(3):249–278, 1993.
R. Weida and D. Litman. Terminological Reasoning with Constraint Networks and an Application to Plan Recognition. In Proceedings of the Third International Conference on Principles of Knowledge Representation and Reasoning (KR'92), Cambridge, Massachusetts, pages 282–293, 1992.
P. Willett. Algorithms for the Calculation of Similarity in Chemical Structure Databases. In M.A. Johnson and G.M. Maggiora, editors, Concepts and Applications of Molecular Similarity, pages 43–63. John Wiley & Sons Ltd, Chichester, West Sussex, 1990.
M.E. Winston, R. Chaffin, and D. Herrmann. A Taxonomy of Part-Whole Relations. Cognitive Science, 11:417–444, 1987.
Author information
Authors and Affiliations
Editor information
Rights and permissions
Copyright information
© 1994 Springer-Verlag Berlin Heidelberg
About this paper
Cite this paper
Napoli, A., Lieber, J. (1994). A first study on case-based planning in organic synthesis. In: Wess, S., Althoff, KD., Richter, M.M. (eds) Topics in Case-Based Reasoning. EWCBR 1993. Lecture Notes in Computer Science, vol 837. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-58330-0_108
Download citation
DOI: https://doi.org/10.1007/3-540-58330-0_108
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-58330-1
Online ISBN: 978-3-540-48655-8
eBook Packages: Springer Book Archive