Computer-assisted synthetic analysis

This work has been carried out in association with Professor Elias J. Corey, who suggested the study of protective groups for use in computer-assisted synthetic analysis. 1 appreciate his continued help and encouragement. I am grateful to Dr. 

Corey EJ, Wipke WT, Cramer RD HI, Howe WJ. Computer-assisted synthetic analysis. Facile man-machine communication of chemical structure by interactive computer graphics. J Am Chem Soc 1972 94 421-30. 

After introducing the algorithm for strategic bond selection developed in connection with "computer-assisted synthetic analysis" (see Part B), we can now return to the use of radical intermediates in the synthesis of monocyclic (and polycyclic) compounds (see Heading 6.1.3). 

Corey EJ, Long AK, Greene TW, Miller JW. Computer-assisted synthetic analysis. Selection of protective groups for multistep organic syntheses. J Org Chem 1985 50 1920-1927. 

Corey EJ, Wipke WT, Cramer RD, Howe WJ (1972) Computer-assisted synthetic analysis. Facile man-machine communication of chemical structure by interactive computer graphics, J Am Chem Soc 94/2 421 Wipke WT, Braun H, Smith G, Choplin F, SieberW (1977) SECS — Simulation and evaluation of chemical synthesis Strategy and planning, in Computer-assisted organic synthesis, Wipke WT, Howe WJ ed, ACS Symposium Series, p 98... 

Organic Syntheses. E. J. Corey, W. T. Wipke, R. D. Cramer, and W. J. Howe,/. Am. Chem. Soc., 94, 421 (1972). Computer-Assisted Synthetic Analysis. Facile Man-Machine Communication of Chemical Structure by Interactive Computer Graphics. E. J. Corey, W. T. Wipke, R. D. Cramer, and H. J. Howe,/. Am. Chem. Soc., 94, 431 (1972). Techniques for Perception by a Computer of Synthetically Significant Structural Features in Complex Molecules. 

The computer-assisted synthetic analysis designated OCSS (organic chemical simulation of synthesis) and LHASA (logic and heuristics applied to synthetic analysis) were designed to assist chemists in synthetic analysis by Corey et LHASA generates trees of synthetic intermediates from a target molecule by analysis in the retrosynthetic direction. 

Computer-Assisted Synthetic Analysis. Quantitative Assessment of Transform Utilities. 

Computer-Assisted Synthetic Analysis The Merck Experience... 

Corey, E.J., Howe, W.J., and Pensak, D.A., Computer-Assisted Synthetic Analysis. Methods for Machine Generation of Synthetic Intermediates Involving Multistep Look-Ahead, J. Am. Chem. Soc., 96, 7724, 1974. 

Frequently, during the experimental realization of a synthetic plan, certain functional groups will interfere with the performance of desired reactions. When this happens, it becomes necessary to protect the offending group (reversibly modify it to some other functionality that is stable to the reaction conditions). The extension of computer assisted synthetic analysis to sophisticated levels necessitates the detection of possible interferences. Such situations must be presented to the chemist in a generally useful manner. 

Computer-Assisted Synthetic Analysis in Drug Research... 

Figure 2, Computer-assisted synthetic analysis types and classes...

Stimulating and valuable to a chemist. The field of computer-assisted synthetic analysis is fascinating in its own right, and surely one of the most interesting problems in the area of machine intelligence. Because of the enormous memory and speed of modern machines and the probability of continuing advances, it seems clear that computers can play an important role in synthetic design. ... 

E. J. Corey and W. L. Jorgensen, Computer-Assisted Synthetic Analysis. Synthetic Strategies Based on Appendages and the Use of Reconnective Transforms , J, Amer. Chem. Soc., 1976, 98, 189. 

The synthetic approach (among others) was suggested by LHASA-10, the Harvard program for computer-assisted synthetic analysis. For some reading see Corey, E. J. Quart. Rev., Chem. Soc. 1971,25, 455. 

Overall this synthesis is quite direct. It is notable that the approach was suggested by a computer-assisted synthetic analysis developed at Harvard. It is also notable that the choice of 1,3-difunctional aminoketone 2 as a late intermediate may have been responsible for recognition of this Mannich reaction strategy. 

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