Construction of functional group reactivity database under various reaction conditions automatically extracted from reaction database in a synthesis design system

Journal of Chemical Information and Modeling

Volumn 50, Issue 3, 2010, Pages 327-338

  Tanaka, Akio ^a   Okamoto, Hideho ^b   Bersohn, Malcolm ^c  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DATABASE SYSTEMS;

REACTION CONDITIONS; REACTION DATABASE; RELATIVE RATES; RELATIVE REACTIVITIES; SYNTHESIS DESIGN;

CHEMICAL REACTIVITY;

ORGANIC COMPOUND;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMPUTER PROGRAM; COMPUTER SIMULATION; FACTUAL DATABASE; SYNTHESIS;

COMPUTER SIMULATION; DATABASES, FACTUAL; MODELS, CHEMICAL; ORGANIC CHEMICALS; SOFTWARE;

EID: 77949820034     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci9004332     Document Type: Article

References (40)

1. Zass, E. Encyclopedia of Computational Chemistry; Schleyer, R. R., Ed.; Wiley: Chichester, U.K., 1998; pp 2402-2420.
2. Todd, M. H. Computer-aided organic synthesis. Chem. Soc. Rev. 2005, 34, 247-266.
3. (a) Gelernter, H. L.; Sanders, A. F.; Larsen, D. L.; Agarwal, K. K.; Boivie, R. H.; Spritzer, G. A.; Searleman, J. E. Empirical Explorations of SYNCHEM. Science 1977, 197, 1041-1049.
4. (b) Hendrickson, G. J. B. Organic Synthesis in the Age of Computers. Angew. Chem., Int. Ed. Engl. 1990, 29, 1286-1295.
5. (c) Funatsu, K.; Sasaki, S. Computer-Assisted Organic Synthesis Design and Reaction Prediction System AIPHOS. Tetrahedron Comput. Method. 1988, 1, 27-37.
6. (d) Ihlenfeldt, W. D.; Gasteiger, J. Computer-Assisted Planning of Organic Syntheses: The Second Generation of Programs. Angew. Chem., Int. Ed. Engl. 1995, 34, 2613-2633.
7. (e) Barone, R.; Attolini, M.; Arbelot, M.; Chanon, M. What To Do With This Reaction? A New Program in the Field of Computer-Aided Synthesis Design - Application to the Diels-Alder Reaction. Eur. J. Org. Chem. 2006, 5184-5190.
8. (f) Law, J.; Zsoldos, Z.; Simon, A.; Reid, D.; Liu, Y.; Khew, S. Y.; Johnson, A. P.; Major, S.; Wade, R. A.; Ando, H. Y. Route Designer: A Retrosynthetic Analysis Tool Utilizing Automated Retrosynthetic Rule Generation. J. Chem. Inf. Model. 2009, 49, 593-602.
9. Corey, E. J.; Wipke, W. T. Computer-Assisted Design of Complex Organic Syntheses. Science 1969, 166, 178-192.
10. Corey, E. J.; Petersson, A. An Algorithm for Machine Perception of Synthetically Significant Rings in Complex Cyclic Organic Structures. J. Am. Chem. Soc. 1972, 94, 460-465.
11. Bersohn, M. Automatic Problem Solving Applied to Synthetic Chemistry. Bull. Chem. Soc. Jpn. 1972, 45, 1897-1903.
12. Dogane, I.; Takabatake, T.; Bersohn, M. Computer-executed synthesis planning, a progress report. Reel. Trav. Chim. Pays-Bas 1992, 111, 291-296.
13. Tanaka, A.; Kawai, T.; Takabatake, T.; Oka, N.; Okamoto, H.; Bersohn, M. Synthesis of an azaspirane via Birch reduction alkylation prompted by suggestions from a computer program. Tetrahedron Lett. 2006, 47, 6733-6737.
14. Corey, E. J.; Orf, H. W.; Pensak, D. A. Computer-Assisted Synthetic Analysis. The Identification and Protection of Interfering Functionality in Machine-Generated Synthetic Intermediates. J. Am. Chem. Soc. 1976, 98, 210-221.
15. Corey, E. J.; Long, A. K.; Greene, T. W.; Miller, J. W. Computer-Assisted Synthetic Analysis. Selection of Protective Groups for Multistep Organic Syntheses. J. Org. Chem. 1985, 50, 1920-1927.
16. Jorgensen, W. L.; Laird, E. R.; Gushurst, A. J.; Fleischer, J. M.; Gothe, S. A.; Helson, H. E.; Paderes, G. D.; Sinclair, S. CAMEO: A program for the logical prediction of the products of organic reactions. Pure Appl. Chem. 1990, 62, 1921-1932.
17. Röse, P.; Gasteiger, J. Automated Derivation of Reaction Rules for the EROS 6.0 System for Reaction Prediction. Anal. Chim. Acta 1990, 235, 163-168.
18. Satoh, H.; Funatsu, K. SOPHIA, a Knowledge Base Guided Reaction Prediction System-Utilization of a Knowledge Base Derived from a Reaction Database. J. Chem. Inf. Comput. Sci. 1995, 35, 34-44.
19. Bersohn, M. The computer derivation of stereochemical relationships from the chirality of ring atoms. J. Chem. Soc., Perkin Trans. 1 1979, 1975-1977.
20. Lewis, N.; Taylor, R. J. K.; Watoson, R. J.; McKillop, A. A Simple and Efficient Procedure for the Preparation of Chiral 2-Oxazolidinones from a-Amino Acides. Synth. Commun. 1995, 25, 561-568.
21. Soai, K.; Yokoyama, S.; Ookawa, A. Reduction of Azides to Amines with Sodium Borohydride in Tetrahydrofuran with Dropwise Addition of Methanol. Synthesis 1987, 48-49.
22. Takikawa, H.; Shimbo, K.; Mori, K. Pheromone Synthesis, CLXXXIII. Synthesis of (1R, 2R, 5S, 7R)- and (lR, 2S, 5S, 7R)-2-hydroxy-exo-Brevi-comin, the Components of the Male-Produced Volatiles of the Mountain Pine Beetle, dendroctonus ponderosae. Liebigs Ann. 1997, 821-824.
23. Varma, R. S.; Kabalka, G. W. Allylic Alcohols Via the Chemoselective Reduction of Enone Systems with Sodium Borohydride in Methanolic Tetrahydrofuran. Synth. Commun. 1985, 75, 985-990.
24. Martin, S. F.; Clark, C. W.; Corbett, J. W. Applications of Vinylogous Mannich Reactions. Asymmetric Synthesis of the Heteroyohimboid Alkaloids (-)-Ajmalicine, (+)-19-epi-Ajmalicine, and (-)-Tetrahy-droalstonine. J. Org. Chem. 1995, 60, 3236-3242.
25. Kapeller, H.; Griengl, H. Synthesis of methyl 5-azido-5-deoxy-2, 3-O-isopropylidenecarba-α-D-allo-hexafuranuronate, the sugar part of carbapolyoxins and carbanikkomycins. Tetrahedron 1997, 53, 14635-14644.
26. Dalby, A.; Nourse, J. G.; Hounshell, W. D.; Gushurst, A. K. I.; Grier, D. L.; Leland, B. A.; Laufer, J. Description of several chemical structure file formats used by computer programs developed at Molecular Design Limited. J. Chem. Inf. Comput. Sci. 1992, 32, 244-255.
27. Benati, L.; Montevecchi, P. C.; Nanni, D.; Spagnolo, P.; Volta, M. Reduction of azides to amines by samarium diiodide. Tetrahedron Lett. 1995, 36, 7313-7314.
28. Maiti, S. N.; Singh, M. P.; Micetich, R. G. Facile conversion of azides to amines. Tetrahedron Lett. 1986, 27, 1423-1424.
29. Hamelin, O.; Greene, A. E.; Depres, J. P.; Declercq, J. P.; Tinant, B. Highly Stereoselective First Synthesis of an A-Ring-Functionalized Bakkane: Novel Free-Radical Approach to 9-Acetoxyfukinanolide. J. Am. Chem. Soc. 1996, 118, 9992-9993.
30. Current Chemical reactions, which is one of reaction databases in ISIS/ Base. Information of the database and system is available via the Internet at http://www.symyx.com/products/databases/synthesis/index.jsp.
31. Sajiki, H. Selective inhibition of benzyl ether hydrogenolysis with Pd/C due to the presence of ammonia, pyridine or ammonium acetate. Tetrahedron Lett. 1995, 36, 3465-3468.
32. Tamagnan, G.; Gao, Y. G.; Bakthavachalam, V.; White, W. L.; Neumeyer, J. L. An efficient synthesis of m-hydroxycocaine and m-hydroxybenzoylecgonine: two metabolites of cocaine. Tetrahedron Lett. 1995, 36, 5861-5864.
33. Back, T. G.; Ghau, J. H. L.; Parvez, M. A Convenient Synthesis of 11-aza-C-homoestranes. Synthesis 1995, 162-164.
34. Boger, D. L.; Mckie, J. A.; Nashi, T.; Ogiku, T. Enantioselective Total Synthesis of (+)-Duocarmycin A, epi-(+)-Duocarmycin A, and Their Unnatural Enantiomers. J. Am. Chem. Soc. 1996, 118, 2301-2302.
35. Dragovich, P. S.; Prins, T. J.; Zhou, R. Palladium Catalyzed, Regioselective Reduction of 1, 2-Epoxides by Ammonium Formate. J. Org. Chem. 1995, 60, 4922-4924.
36. Kim, Y. M.; Kim, D. H. Convenient Preparation of AU Four Possible Stereoisomers of 2-Benzyl-3, 4-epoxybutanoic Acid, Pseudomecha-nism-based inactivator for Carboxypeptidase A via α-Chymotrypsin-Catalyzed Hydrolysis. Bull. Korean Chem. Soc. 1996, 17, 967-969.
37. Zhao, W. M.; Wan, X. Y. A Practical Synthesis of 4-(3', 4'-Dihydroxylphenyl)-l, 2, 3, 4-tetrahydroisoquinoline. Org. Prep. Proced. Int. 1995, 27, 513-516.
38. Xia, X. Y.; Wang, J. Y.; Hager, M. W.; Sisti, N.; Liotta, D. C. Stereocontrolled synthesis of β-2'-deoxypyrimidine nucleosides via intramolecular glycosylations. Tetrahedron Lett. 1997, 38, 1111-1114.
39. Baldwin, J. E.; Fryer, A. M.; Spyvee, M. R.; Whitehead, R. C.; Wood, M. E. Stereocontrol in the synthesis of kainoids. Tetrahedron Lett. 1996, 37, 6923-6924.
40. Martin, S. F.; Clark, C. W.; Corbett, J. W. Applications of Vinylogous Mannich Reactions. Asymmetric Synthesis of the Heteroyohimboid Alkaloids (-)-Ajmalicine, (+)-19-epi-Ajmalicine, and (-)-Tetrahy-droalstonine. J. Org. Chem. 1995, 60, 3236-3242.