Synthesis computer-assisted synthetic analysis

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, 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... 

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. 

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. 

Computer-assisted analysis of complex synthetic problems, Q. Rev. 1971, 25, 455 (c) E.J. Corey, A.K. Long, S.D. Rubenstein, Computer-assisted analysis in organic synthesis. Science 1985, 228, 408. 

There are a number of computer programs which can assist the synthetic chemist in the retrosynthetic analysis of a target compound. One that is specifically designed to be applied to the synthesis of chiral compounds is the CHIRON program, developed at the University of Montreal by Professor Steve Hanessian. CHIRON does not generate a full retrosynthetic tree but rather yields readily available starting materials from the Chiral Poof that contain the chirality needed to construct the product in optically pure form. 

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