A first study on case-based planning in organic synthesis

  • Amedeo Napoli
  • Jean Lieber
Selected Papers Case-Based Design
Part of the Lecture Notes in Computer Science book series (LNCS, volume 837)


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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    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.Google Scholar
  2. 2.
    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.Google Scholar
  3. 3.
    E.J. Corey and X.M. Cheng. The Logic of Chemical Synthesis. John Wiley & Sons, New York, 1989.Google Scholar
  4. 4.
    E.J. Corey, A.K. Long, and S.D. Rubenstein. Computer-Assisted Analysis in Organic Synthesis. Science, 228:408–418, 1985.Google Scholar
  5. 5.
    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.Google Scholar
  6. 6.
    J. Lieber. Étude du raisonnement par cas. Rapport de Recherche 93-R-043, Centre de Recherche en Informatique de Nancy, 1993.Google Scholar
  7. 7.
    G. Masini, A. Napoli, D. Colnet, D. Léonard, and K. Tombre. Object-Oriented Languages. Academic Press, London, 1991.Google Scholar
  8. 8.
    J. Mostow. Design by Derivational Analogy: Issues in the Automated Replay of Design Plans. Artificial Intelligence, 40:119–184, 1989.Google Scholar
  9. 9.
    A. Napoli. Using Frame-Based Representation Languages to Describe Chemical Objects. New Journal of Chemistry, 14(12):913–919, 1990.Google Scholar
  10. 10.
    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.Google Scholar
  11. 11.
    B. Nebel. Reasoning and Revision in Hybrid Representation Systems. Lecture Notes in Computer Science 422. Springer-Verlag, Berlin, 1990.Google Scholar
  12. 12.
    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.Google Scholar
  13. 13.
    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.Google Scholar
  14. 14.
    L.G. Shapiro and R.M. Haralick. Structural Descriptions and Inexact Matching. IEEE Transactions on Pattern Analysis and Machine Intelligence, 3:504–519, 1981.Google Scholar
  15. 15.
    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.Google Scholar
  16. 16.
    M.M. Veloso and J.G. Carbonell. Derivational Analogy in Prodigy: Automating Case Acquisition, Storage, and Utilization. Machine Learning, 10(3):249–278, 1993.Google Scholar
  17. 17.
    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.Google Scholar
  18. 18.
    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.Google Scholar
  19. 19.
    M.E. Winston, R. Chaffin, and D. Herrmann. A Taxonomy of Part-Whole Relations. Cognitive Science, 11:417–444, 1987.Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1994

Authors and Affiliations

  • Amedeo Napoli
    • 1
  • Jean Lieber
    • 1
  1. 1.CRIN CNRS-INRIA LorraineVandœuvre-lès-Nancy CedexFrance

Personalised recommendations