Hunter: A conformational search program for acyclic to polycyclic molecules with special emphasis on stereochemistry

Journal of Computational Chemistry

Volumn 18, Issue 10, 1997, Pages 1264-1281

  Weiser, Jörg ^a,b   Holthausen, Max C ^a,c   Fitjer, Lutz ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b Columbia University ^*  (United States)

^c EMORY UNIVERSITY   (United States)

Author keywords

Conformational search; MM3; MMP2; Modified corner flapping; Stereochemical analysis

Indexed keywords

EID: 0001410695     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-987X(19970730)18:10<1264::AID-JCC2>3.0.CO;2-L     Document Type: Article

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33. For some recent examples, see: (a) L. Fitjer, R. Gerke, and T. Anger, Synthesis, 893 (1994); (b) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron, 50, 10867 (1994); (c) L. Fitjer, B. Rissom, A. Kanschik, and E. Egert, Tetrahedron, 50, 10879 (1994); (d) L. Fitjer, M. Majewski, and H. Monzó-Oltra, Tetrahedron, 51, 8835 (1995).
34. For some recent examples, see: (a) L. Fitjer, R. Gerke, and T. Anger, Synthesis, 893 (1994); (b) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron, 50, 10867 (1994); (c) L. Fitjer, B. Rissom, A. Kanschik, and E. Egert, Tetrahedron, 50, 10879 (1994); (d) L. Fitjer, M. Majewski, and H. Monzó-Oltra, Tetrahedron, 51, 8835 (1995).
35. For some recent examples, see: (a) L. Fitjer, R. Gerke, and T. Anger, Synthesis, 893 (1994); (b) L. Fitjer, A. Kanschik, and M. Majewski, Tetrahedron, 50, 10867 (1994); (c) L. Fitjer, B. Rissom, A. Kanschik, and E. Egert, Tetrahedron, 50, 10879 (1994); (d) L. Fitjer, M. Majewski, and H. Monzó-Oltra, Tetrahedron, 51, 8835 (1995).
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42. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
43. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
44. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
45. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
46. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
47. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
48. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
49. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
50. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
51. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
52. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
53. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
54. For an excellent review, see: (a) K. B. Lipkowitz and M. A. Peterson, Chem. Rev., 93, 2463 (1993). Selected applications: search for the most stable diastereomer: (b) M. Saunders, Science, 253, 330 (1991); (c) P. Tarakeshwar, J. Iqbal, and S. Manogaran, Tetrahedron, 47, 297 (1991). Modeling of diastereomeric transition states: (d) L. F. Tietze, H. Geissler, J. Fennen, T. Brumby, S. Brand, and G. Schulz, J. Org. Chem., 59, 182 (1994); (e) K. Takatori, M. Kajiwara, Y. Sakamoto, T. Shimayama, H. Yamada, and T. Takahashi, Tetrahedron Lett., 35, 5669 (1994). Modeling of inversion processes: (f) A. Peyman and H.-D. Beckhaus, J. Comp. Chem., 13, 541 (1992); (g) I. Kolossváry and W. C. Guida, J. Mol. Struct. (Theochem), 308, 91 (1994); (h) J. H. Brown and C. H. Bushweller, J. Phys. Chem., 98, 11411 (1994). Modeling of conformationally controlled reactions: (i) J. M. Goodman, S. D. Kahn, and I. Paterson, J. Org. Chem., 55, 3295 (1990); (j) T. Takahashi, H. Yokoyama, H. Yamada, T. Haino, and Y. Fukazawa, Synlett, 7, 494 (1993); (k) M. P. Polovinka, D. V. Korchagina, Y. V. Gatilov, I. Y. Bagrianskaya, V. A. Barkhash, V. V. Shcherbukhin, N. S. Zefirov, V. B. Perutskii, N. D. Ungur, and P. F. Vlad, J. Org. Chem., 59, 1509 (1994); (l) H. Suginome, T. Kondoh, C. Gogonea, V. Singh, H. Goto, and E. Osawa, J. Chem. Soc. Perkin Trans, 1, 69 (1995); (m) L. Fitjer, A. Malich, C. Paschke, S. Kluge, R. Gerke, B. Rissom, J. Weiser, and M. Noltemeyer, J. Am. Chem. Soc., 117, 9180 (1995).
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82. For applications, see: (a) R. A. Donnelly, Chem. Phys. Lett., 136, 274 (1987); (b) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, Tetrahedron Lett., 29, 4373 (1988); (c) J. W. Moskowitz, K. E. Schmidt, S. R. Wilson, and W. Cui, Int. J. Quant. Chem. Quant. Chem. Symp., 22, 611 (1988); (d) R. H. J. M. Otten and L. P. P. P. van Ginneken, The Annealing Algorithm, Kluwer, Boston, 1989; (e) M. T. Barakat and P. M. Dean, J. Comput.-Aided Molec. Design, 4, 295 (1990); (f) I. M. Navon, F. B. Brown, and D. H. Robertson, Computers Chem., 14, 305 (1990); (g) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, J. Comput. Chem., 12, 342 (1991); (h) S. H. Nilar, J. Comput. Chem., 12, 1008 (1991); (i) F. Guarnieri and S. R. Wilson, Tetrahedron, 48, 4271 (1992); (j) M. E. Snow, J. Comput. Chem., 13, 579 (1992), and Ref. 13b.
83. For applications, see: (a) R. A. Donnelly, Chem. Phys. Lett., 136, 274 (1987); (b) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, Tetrahedron Lett., 29, 4373 (1988); (c) J. W. Moskowitz, K. E. Schmidt, S. R. Wilson, and W. Cui, Int. J. Quant. Chem. Quant. Chem. Symp., 22, 611 (1988); (d) R. H. J. M. Otten and L. P. P. P. van Ginneken, The Annealing Algorithm, Kluwer, Boston, 1989; (e) M. T. Barakat and P. M. Dean, J. Comput.-Aided Molec. Design, 4, 295 (1990); (f) I. M. Navon, F. B. Brown, and D. H. Robertson, Computers Chem., 14, 305 (1990); (g) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, J. Comput. Chem., 12, 342 (1991); (h) S. H. Nilar, J. Comput. Chem., 12, 1008 (1991); (i) F. Guarnieri and S. R. Wilson, Tetrahedron, 48, 4271 (1992); (j) M. E. Snow, J. Comput. Chem., 13, 579 (1992), and Ref. 13b.
84. For applications, see: (a) R. A. Donnelly, Chem. Phys. Lett., 136, 274 (1987); (b) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, Tetrahedron Lett., 29, 4373 (1988); (c) J. W. Moskowitz, K. E. Schmidt, S. R. Wilson, and W. Cui, Int. J. Quant. Chem. Quant. Chem. Symp., 22, 611 (1988); (d) R. H. J. M. Otten and L. P. P. P. van Ginneken, The Annealing Algorithm, Kluwer, Boston, 1989; (e) M. T. Barakat and P. M. Dean, J. Comput.-Aided Molec. Design, 4, 295 (1990); (f) I. M. Navon, F. B. Brown, and D. H. Robertson, Computers Chem., 14, 305 (1990); (g) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, J. Comput. Chem., 12, 342 (1991); (h) S. H. Nilar, J. Comput. Chem., 12, 1008 (1991); (i) F. Guarnieri and S. R. Wilson, Tetrahedron, 48, 4271 (1992); (j) M. E. Snow, J. Comput. Chem., 13, 579 (1992), and Ref. 13b.
85. For applications, see: (a) R. A. Donnelly, Chem. Phys. Lett., 136, 274 (1987); (b) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, Tetrahedron Lett., 29, 4373 (1988); (c) J. W. Moskowitz, K. E. Schmidt, S. R. Wilson, and W. Cui, Int. J. Quant. Chem. Quant. Chem. Symp., 22, 611 (1988); (d) R. H. J. M. Otten and L. P. P. P. van Ginneken, The Annealing Algorithm, Kluwer, Boston, 1989; (e) M. T. Barakat and P. M. Dean, J. Comput.-Aided Molec. Design, 4, 295 (1990); (f) I. M. Navon, F. B. Brown, and D. H. Robertson, Computers Chem., 14, 305 (1990); (g) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, J. Comput. Chem., 12, 342 (1991); (h) S. H. Nilar, J. Comput. Chem., 12, 1008 (1991); (i) F. Guarnieri and S. R. Wilson, Tetrahedron, 48, 4271 (1992); (j) M. E. Snow, J. Comput. Chem., 13, 579 (1992), and Ref. 13b.
86. For applications, see: (a) R. A. Donnelly, Chem. Phys. Lett., 136, 274 (1987); (b) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, Tetrahedron Lett., 29, 4373 (1988); (c) J. W. Moskowitz, K. E. Schmidt, S. R. Wilson, and W. Cui, Int. J. Quant. Chem. Quant. Chem. Symp., 22, 611 (1988); (d) R. H. J. M. Otten and L. P. P. P. van Ginneken, The Annealing Algorithm, Kluwer, Boston, 1989; (e) M. T. Barakat and P. M. Dean, J. Comput.-Aided Molec. Design, 4, 295 (1990); (f) I. M. Navon, F. B. Brown, and D. H. Robertson, Computers Chem., 14, 305 (1990); (g) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, J. Comput. Chem., 12, 342 (1991); (h) S. H. Nilar, J. Comput. Chem., 12, 1008 (1991); (i) F. Guarnieri and S. R. Wilson, Tetrahedron, 48, 4271 (1992); (j) M. E. Snow, J. Comput. Chem., 13, 579 (1992), and Ref. 13b.
87. For applications, see: (a) R. A. Donnelly, Chem. Phys. Lett., 136, 274 (1987); (b) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, Tetrahedron Lett., 29, 4373 (1988); (c) J. W. Moskowitz, K. E. Schmidt, S. R. Wilson, and W. Cui, Int. J. Quant. Chem. Quant. Chem. Symp., 22, 611 (1988); (d) R. H. J. M. Otten and L. P. P. P. van Ginneken, The Annealing Algorithm, Kluwer, Boston, 1989; (e) M. T. Barakat and P. M. Dean, J. Comput.-Aided Molec. Design, 4, 295 (1990); (f) I. M. Navon, F. B. Brown, and D. H. Robertson, Computers Chem., 14, 305 (1990); (g) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, J. Comput. Chem., 12, 342 (1991); (h) S. H. Nilar, J. Comput. Chem., 12, 1008 (1991); (i) F. Guarnieri and S. R. Wilson, Tetrahedron, 48, 4271 (1992); (j) M. E. Snow, J. Comput. Chem., 13, 579 (1992), and Ref. 13b.
88. For applications, see: (a) R. A. Donnelly, Chem. Phys. Lett., 136, 274 (1987); (b) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, Tetrahedron Lett., 29, 4373 (1988); (c) J. W. Moskowitz, K. E. Schmidt, S. R. Wilson, and W. Cui, Int. J. Quant. Chem. Quant. Chem. Symp., 22, 611 (1988); (d) R. H. J. M. Otten and L. P. P. P. van Ginneken, The Annealing Algorithm, Kluwer, Boston, 1989; (e) M. T. Barakat and P. M. Dean, J. Comput.-Aided Molec. Design, 4, 295 (1990); (f) I. M. Navon, F. B. Brown, and D. H. Robertson, Computers Chem., 14, 305 (1990); (g) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, J. Comput. Chem., 12, 342 (1991); (h) S. H. Nilar, J. Comput. Chem., 12, 1008 (1991); (i) F. Guarnieri and S. R. Wilson, Tetrahedron, 48, 4271 (1992); (j) M. E. Snow, J. Comput. Chem., 13, 579 (1992), and Ref. 13b.
89. For applications, see: (a) R. A. Donnelly, Chem. Phys. Lett., 136, 274 (1987); (b) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, Tetrahedron Lett., 29, 4373 (1988); (c) J. W. Moskowitz, K. E. Schmidt, S. R. Wilson, and W. Cui, Int. J. Quant. Chem. Quant. Chem. Symp., 22, 611 (1988); (d) R. H. J. M. Otten and L. P. P. P. van Ginneken, The Annealing Algorithm, Kluwer, Boston, 1989; (e) M. T. Barakat and P. M. Dean, J. Comput.-Aided Molec. Design, 4, 295 (1990); (f) I. M. Navon, F. B. Brown, and D. H. Robertson, Computers Chem., 14, 305 (1990); (g) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, J. Comput. Chem., 12, 342 (1991); (h) S. H. Nilar, J. Comput. Chem., 12, 1008 (1991); (i) F. Guarnieri and S. R. Wilson, Tetrahedron, 48, 4271 (1992); (j) M. E. Snow, J. Comput. Chem., 13, 579 (1992), and Ref. 13b.
90. For applications, see: (a) R. A. Donnelly, Chem. Phys. Lett., 136, 274 (1987); (b) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, Tetrahedron Lett., 29, 4373 (1988); (c) J. W. Moskowitz, K. E. Schmidt, S. R. Wilson, and W. Cui, Int. J. Quant. Chem. Quant. Chem. Symp., 22, 611 (1988); (d) R. H. J. M. Otten and L. P. P. P. van Ginneken, The Annealing Algorithm, Kluwer, Boston, 1989; (e) M. T. Barakat and P. M. Dean, J. Comput.-Aided Molec. Design, 4, 295 (1990); (f) I. M. Navon, F. B. Brown, and D. H. Robertson, Computers Chem., 14, 305 (1990); (g) S. R. Wilson, W. Cui, J. W. Moskowitz, and K. E. Schmidt, J. Comput. Chem., 12, 342 (1991); (h) S. H. Nilar, J. Comput. Chem., 12, 1008 (1991); (i) F. Guarnieri and S. R. Wilson, Tetrahedron, 48, 4271 (1992); (j) M. E. Snow, J. Comput. Chem., 13, 579 (1992), and Ref. 13b.
91. (a) U. Shmueli, S. Carmely, A. Groweiss, and Y. Kashman, Tetrahedron Lett., 22, 709 (1981).
92. Systematic name: decahydro-2,2,5a,7-tetramethyl-6-[2-(1,2,3,3a,4,5,8,8a-octahydro-1-hydroxy-1,4, 4,6-tetramethyl-5-azulenyl)-ethyl] - 1-benzoxepin-3,7-diol-3-acetate. We have taken the trivial name from: (b) S. Carmely and Y. Kashman, J. Org. Chem., 48, 3517 (1983).
93. I. Kolossváry and W. C. Guida, J. Am. Chem. Soc., 115, 2107 (1993), and Ref. 5e, 12b, and 29b.
94. The maximum optimization time for each run of the local optimizers followed from a series of preliminary calculations and was chosen so as to avoid wasting CPU time due to unsuccessful optimizations.
95. The calculations were performed at the Gesellschaft für wissenschaftliche Datenverarbeitung mbH, Göttingen (GWDG).
96. We originally located sipholenol-A monoacetate (13) as interesting test case for a conformational search in Molecular Structures and Dimensions, University Press, Cambridge, Vol. 13, 1982, p. 109 and D97. After the calculations had been completed, we became aware of the fact that no crystal structure data had been deposited and that the data no longer exist (personal communication from U. Shmueli, University of Tel-Aviv). We apologize for this fact.
97. The ball-and-stick model was made with the assistance of SCHAKAL: E. Keller, Chem. Unserer Zeit, 6, 178 (1986).
98. (a) K. B. Wiberg and M. A. Murcko, J. Am. Chem. Soc., 110, 8029 (1988);
99. (b) S. Tsuzuki, L. Schäfer, H. Goto, E. D. Jemmis, H. Hosoya, K. Siam, K. Tanabe, and E. Osawa, J. Am. Chem. Soc., 113, 4665 (1991), and Ref. 9.
100. On the contrary, spot checks revealed several cases where two conformations were defined different by MM3(92), but identical by HUNTER. In these cases the energy difference exceeded diff, whereas the dihedral angles did not differ by more than 2°.
101. J. Weiser, O. Golan, L. Fitjer, and S. E. Biali, J. Org. Chem., 61, 8277 (1996).
102. D. Strobl, J. Weiser, and L. Fitjer, Tetrahedron, 53, 2767 (1997).
103. HUNTER for MM3 (Unix) and SERVANT (Dos), QCPE #674, Quantum Chemistry Program Exchange (QCPE), University of Indiana, Bloomington, IN 47405.