Computational investigations of carbenium ion reactions relevant to sterol biosynthesis

Journal of the American Chemical Society

Volumn 119, Issue 44, 1997, Pages 10846-10854

  Jenson, Corky ^a   Jorgensen, William L ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICHLOROMETHANE; LANOSTEROL SYNTHASE; METHANOL; SOLVENT;

ARTICLE; COMPUTER SIMULATION; CYCLIZATION; STEROL SYNTHESIS;

EID: 0030781006     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9714245     Document Type: Article

References (56)

1. (a) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890. (b) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (c) van Tamelen, E. E. Acc. Chem. Res. 1968, 1, 111. (d) Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
2. (a) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890. (b) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (c) van Tamelen, E. E. Acc. Chem. Res. 1968, 1, 111. (d) Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
3. (a) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890. (b) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (c) van Tamelen, E. E. Acc. Chem. Res. 1968, 1, 111. (d) Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
4. (a) Eschenmoser, A.; Ruzicka, L.; Jeger, O.; Arigoni, D. Helv. Chim. Acta 1955, 38, 1890. (b) Johnson, W. S. Acc. Chem. Res. 1968, 1, 1. (c) van Tamelen, E. E. Acc. Chem. Res. 1968, 1, 111. (d) Abe, I.; Rohmer, M.; Prestwich, G. D. Chem. Rev. 1993, 93, 2189.
5. (a) Corey, E. J.; Virgil, S. C.; Sarshar, S. J. Am. Chem. Soc. 1991, 113, 8171.
6. (b) Krief, A.; Scauder, J.-R.; Guittet, E.; Herve du Penhoat, C.; Lallemand, J.-Y. J. Am. Chem. Soc. 1987, 709, 7910.
7. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025.
8. Corey, E. J.; Virgil, S. C.; Cheng, H.; Baker, C. H.; Matsuda, S. P. T.; Singh, V.; Sarshar, S. J. Am. Chem. Soc. 1995, 117, 11819.
9. (e) Corey, E. J.; Cheng, H.; Baker, C. H.; Matsuda, S. P. T.; Li, D.; Song, X. J. Am. Chem. Soc. 1997, 119, 1277.
10. (f) Corey, E. J.; Cheng, H..; Baker, C. H.; Matsuda, S. P. T.; Li, D.; Song, X. J. Am. Chem. Soc. 1997, 119, 1289.
11. (a) Nishizawa, M.; Takenaka, H.; Hayashi, Y. J. Org. Chem. 1986, 57, 806.
12. (b) Pock, R.; Mayr, H.; Rubow, M.; Wilhelm, E. J. Am. Chem. Soc. 1986, 108, 7767.
13. Taylor, S. K. Org. Prep. Proced. Int. 1992, 24, 247.
14. Barrero, A. F.; Altarejos, J.; Alvarez-Manzaneda, E. J.; Ramos, J. M.; Salido, S. J. Org. Chem. 1996, 61, 2215.
15. (e) Corey, E. J.; Wood, H. B., Jr. J. Am. Chem. Soc. 1996, 118, 11982.
16. (f) Tietze, L. F. Chem. Rev. 1996, 96, 115.
17. (g) Li, T.; Lerner, R. A.; Janda, K. D. Acc. Chem. Res. 1997, 30, 115.
18. Nishizawa, M.; Takenaka, H.; Hayashi, Y. J. Am. Chem. Soc. 1985, 707, 522.
19. (a) Sauers, C. K. Ph.D. Thesis University of Illinois, Urbana, IL, 1957.
20. (b) Johnson, W. S.; Owyang, R. J. Am. Chem. Soc. 1964, 86, 5593.
21. Frisch, M. J.; Trucks, G. W.; Head-Gordon, M; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian94, Revision A; Gaussian, Inc.; Pittsburgh, PA, 1994.
22. (a) Jorgensen, W. L.; Blake, J. F.; Lim D.; Severance, D. L. Trans. Faraday Soc. 1994, 90, 1727.
23. (b) Jones-Hertzog, D. K.; Jorgensen, W. L. J. Am. Chem. Soc. 1995, 117, 9077.
24. (a) Jorgensen, W. L. J. Phys. Chem. 1986, 90, 1276.
25. (b) Briggs, J. M.; Matsui, T.; Jorgensen, W. L. J. Comput. Chem. 1990, 11, 958.
26. Lim, D.; Hrovat, D. A.; Borden, W. T.; Jorgensen, W. L. J. Am. Chem. Soc. 1994, 116, 3494.
27. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. J. Am. Chem. Soc. 1996, 118, 11225.
28. (a) Zwanzig, R. W. J. Chem. Phys. 1954, 22, 1420.
29. (b) Jorgensen, W. L.; Ravimohan, C. J. Chem. Phys. 1985, 83, 3050.
30. Jorgensen, W. L. BOSS, Version 3.6; Yale University: New Haven, CT, 1995.
31. Press, W. H.; Teukolsky, S. A.; Vettering, W. T.; Flannery, B. P. Numerical Recipes in FORTRAN, 2nd ed.; Cambridge Univ. Press: Cambridge, U.K., 1992.
32. Fry, J. L.; Engler, E., M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1972, 94, 4628.
33. -1 were treated as rotations for computing ΔH298.
34. (a) Sieber, S.; Buzek, P.; Schleyer, P. v. R.; Koch, W.; Carniero, J. W. M. J. Am. Chem. Soc. 1993, 115, 259.
35. (b) Ibrahim, M. R.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 819.
36. Schultz, J. C.; Houle, F. A.; Beauchamp, J. L. J. Am. Chem. Soc. 1984, 106, 3917.
37. Bittner, E. W.; Arnett, E. M.; Saunders, M. J. Am. Chem. Soc. 1976, 98, 3734.
38. Saunders, M.; Lloyd, J. R. J. Am. Chem. Soc. 1977, 99, 7090.
39. Wiberg, K. B.; Schleyer, P. v. R.; Streitwieser, A. Can. J. Chem. 1996, 74. 892.
40. Schreiner, P. R.; Severance, D. L.; Jorgensen, W. L.; Schleyer, P. v. R.; Schaefer, H. F., III J. Am. Chem. Soc. 1995, 117, 2663.
41. Mayr, H.; Förner, W.; Schleyer, P. v. R.. J. Am. Chem. Soc. 1979, 101, 6032. Coumoyer, M. E.; Jorgensen, W. L. . J. Am. Chem. Soc. 1984, 106, 5104.
42. Mayr, H.; Förner, W.; Schleyer, P. v. R.. J. Am. Chem. Soc. 1979, 101, 6032. Coumoyer, M. E.; Jorgensen, W. L. . J. Am. Chem. Soc. 1984, 106, 5104.
43. Saunders, M.; Jiménez-Vázquez, H. A. Chem. Rev. 1991, 91, 375.
44. (a) Buntel, C. J.; Griffin, J. H. J. Am. Chem. Soc. 1992, 114, 9711.
45. (b) Zheng, S.; Buntel, C. J.; Griffin, J. H. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7370.
46. Buntel, C. J.; Griffin, J. H. In Isopentenoids and Other Natural Products, Evolution and Function; Nes, W. D., Ed.; ACS Symposium Series 562; American Chemical Society; Washington, DC, 1994.
47. Baker, C. H.; Matsuda, S. P. T.; Liu, D. R.; Corey, E. J. Biochem. Biophys. Res. Commun. 1995, 213, 154.
48. (a) Dodd, D. S.; Oehlschlager, A. C.; Georgopapadakou, N. H.; Polak, A.-M.; Hartman, P. G. J. Org. Chem. 1992, 57, 7226.
49. (b) Abe, I.; Prestwich, G. D. Lipids 1995, 30, 231.
50. Zheng, Y. F; Dodd, D. S.; Oehlschlager, A. C. Tetrahedron 1995, 51, 5255.
51. Goldman, R. C.; Zakula, D.; Capobianco, J. O.; Sharpe, B. A.; Griffin, J. H. Antimicrob. Agents Chemother. 1996, 40, 1044.
52. Johnson, W. S.; Lindell, S. D.; Steele, J. J. Am. Chem. Soc. 1987, 109, 5852.
53. Dougherty, D. A. Science 1996, 271, 163.
54. Kumpf, R. A.; Dousherty, D. A. Science 1993, 261, 1708. Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 4177.
55. Kumpf, R. A.; Dousherty, D. A. Science 1993, 261, 1708. Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 4177.
56. Schleyer, P. v. R.; Buzek, P.; Müller, T.; Apeloig, Y.; Siehl, H.-U. Angew. Chem., Int. Ed. Engl. 1993, 32, 1471.