The psychobiological basis of heuristic synthesis planning—man, machine and the chiron approach

Pure and Applied Chemistry

Volumn 62, Issue 10, 1990, Pages 1887-1910

  Hanessian, Stephen ^a   Franco, Jonathan ^a   Larouche, Benoit ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84950084793     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/pac199062101887     Document Type: Article

References (41)

1. L.A. Paquette and T. Sugimura, J. Am. Chem. Soc. 108. 3841 (1986).
2. W. Oppolzer and K. Thirring, J. Am. Chem. Soc. 104. 4978 (1982).
3. E.J. Corey, P. Da Silva Jardine and J.C. Rohloff, J. Am. Chem. Soc. 110.3672 (1988); For the use of a-ionone, see also, E.R. Koft, A.S. Kotnis and T.A. Broadbent, Tetrahedron Lett. 28, 2799 (1987); K.C. Nicolaou and W.S. Li, JCS. Chem. Comm. 425 (1985)
4. M. Kinoshita, A. Hagiwara and S. Aburaki, Bull. Chem. Soc. Japan. 48, 570
5. T. Kitahara and K. Mori, Tetrahedron. 40, 2935 (1984).
6. J.P.H. Verheyden, A.C. Richardson, R.S. Bhatt, B.D. Grant, W.L. Fitch and J.G. Moffatt, Tetrahedron. 40. 2935 (1984).
7. M.P. Edwards, S.V. Ley, S.G. Lister, B.D. Palmer and D.J. Williams, J. Org. Chem. 49, 3503 (1984).
8. E.J. Corey and H.L. Pearce, J. Am. Chem. Soc. 101. 5841 (1979).
9. B. Edwards, Drawing on the Right Side of the Brain. J.P. Tarcher, Inc., Los Angeles (1989).
10. J. Levy, “Differential Perceptual Capacities in Major and Minor Hemispheres”, Proc. Nat. Acad. Sci. USA. 61, 1151 (1968); “Psychobiological Implications of Bilateral Asymmetry” in Hemisphere Function and the Human Brain. S.J. Dimond, J.G. Beaumont Ed., John Wiley & Sons, N.Y. (1974).
11. I. Hargittai, M. Hargittai, Symmetry through the Eyes of a Chemist. VCH, Weinheim, Federal Republic of Germany (1986).
12. See reference 32; for other syntheses and approaches to forskolin see, S. Hashimoto, S. Sakata, M. Sonegawa and S. Ikegami, J. Am. Chem. Soc. 110. 3670 (1988); F.E. Ziegler, B.H. Jaynes and M.T. Saindane, J. Am. Chem. Soc. 109. 8115 (1987) and references cited therein.
13. S. Hanessian, P. Roy, P.A. Hodges, M. Petrin, R. Di Fabio and G. Carganico, J. Org. Chem. in press.
14. See for example, S. Mzengeza, R.A. Whitney, R.C. Kelly, I. Schletter, S.J. Stein and W. Wierenga, J. Am. Chem. Soc. 101. 1054 (1979); J.E. Baldwin, J.K. Cha, and L.I. Kruse, Tetrahedron Lett. 41, 5241
15. K. Mori, Tetrahedron. 30, 4223 (1974).
16. W.C. Still, S. Murata, G. Revial and K. Yushihara, J. Am. Chem. Soc. 105. 625 (1983).
17. J.H. Hutchinson and T. Money, Can. J. Chem. 63, 3182 (1985).
18. S. Hanessian, J. Franco, G. Gagnon, D. Laramee and B. Larouche, J. Chem. Inf. Comput. Sci. in press; See also The Chiron Manual, version 4.2 (1990).
19. For examples of the use of the Chiron Program, see S. Hanessian, in Organic Synthesis - An Interdisciplinary Challenge. Proc. 5th IUPAC Symposium on Organic Synthesis, J. Streith, H. Prinsbach, G. Schill, Eds. Freiburg, FRG, Aug. 27, pp. 267–279 (1984); S. Hanessian and D. Desilets, in Trends in Med. Chem. H. van der Groot, L. Pallos, G. Domany and H. Timmerman Eds. Elsevier, Amsterdam, 165 (1988); S. Hanessian, A.-M. Faucher and S. Leger, Tetrahedron. 46, 231 (1990); S. Hanessian, Y. Sakito, D. Dhanoa and L. Baptistella, Tetrahedron. 46, 6623 (1989).
20. J.H. Hutchinson, T. Money and S.E. Piper, Can. J. Chem. 64, 854 (1986).
21. For an excellent review, see Money, T. Nat. Prod. Rep. 2, 253 (1985).
22. M. Rowley, M. Tsukamoto and Y. Kishi, J. Am. Chem. Soc. 111. 2735 (1989).
23. For a related example, see, R.K. Boeckman Jr., A. Arranitis and M.E. Voss, J. Am. Chem. Soc. 111. 2739 (1989).
24. R.K. Boeckman Jr., D.M. Blum and S.D. Arthur, J. Am. Chem. Soc. 101. 5060 (1979).
25. E.J. Corey, B. De, J.W. Ponder and J.M. Berg, Tetrahedron Lett. 26, 1015 (1984).
26. T.K. Jones, S.G. Mills, R.A. Reamer, D. Askin, R. Desmond, R.P. Volante and I. Shinkai, J. Am. Chem. Soc., Ill, 1157 (1989).
27. H. Kaga, S. Kobayashi and M. Ohno, Tetrahedron Lett. 30, 113 (1989).
28. N. Kato, H. Kataoka, S. Ohbuchi, S. Tanaka and H. Takeshita, JCS Chem. Comm. 354 (1988).
29. For a recent synthesis of optically pure meroquinene, see R.T. Brown and J. Leonard, JCS Chem. Comm. 725 (1978) and references cited therein.
30. S. Hanessian, A.-M. Faucher and S. Leger, Tetrahedron. 46, 231 (1990).
31. For the use of a bicyclic template, see a. A.E. Greene, M.J. Luche and A.A. Serra, J. Org. Chem. 50, 3957 (1985); b. M. Shibasaki, M. Yamazaki, K. Iseki and S. Ikegami, Tetrahedron Lett. 23, 5311 (1982).
32. We thank Dr. C. Fehr at Firmenich, S.A. Geneva Switzerland for suggesting this target molecule.
33. G. Biichi and C. Mak, J. Am. Chem. Soc. 99, 8073 (1977).
34. M.M. Ponpipom, B.Z. Yue, R.L. Bugianesi, D.R. Brooker, M.N. Chang and T.Y. Shen, Tetrahedron Lett. 27, 309 (1986).
35. A.I. Meyers, L.M. Fuentes, M. Bos and D.A. Dickman, Chemica Scripta. 25, 25 (1985).
36. A.K. Long, S. D. Rubenstein and L.J. Joncas, Chem. Eng. News. 61, 22 (1983).
37. T.D. Salatin and W.L. Jorgensen, J. Org. Chem. 46, 2043 (1980).
38. W.T. Wipke, G.I. Ouchi and S. Krishnan, Artif. Intell. 11, 173 (1978); N.T. Wipke and D. Rogers, J. Chem. Inf, Comput. Sci., 24, 71 (1984).
39. J. Gasteiger and C. Jochum, Top Curr. Chem. 93 (1978).
40. J.B. Hendrickson, D.L. Grier and A.G. Toczko, J. Am. Chem. Soc. 107. 5228 (1985).
41. For an excellent recent summary, see N.J. Hrib, Ann. Rep. Med. Chem. 21, 303 (1986).