Diels-Alder reactions of amino acid-derived trienes

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5930-5940

  Murray, William V ^a   Sun, Sengen ^a   Turchi, Ignatius J ^a   Brown, Frank K ^a   Gauthier, A Diane ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENYLALANINE DERIVATIVE; VALINE;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033529894     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990459f     Document Type: Article

References (30)

1. For the syntheses of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Gutierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4336. (b) Moriwake, T.; Hamano, S.; Saito, S.; Torii, S. J. Org. Chem. 1988, 54, 4114. (c) Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1988, 48, 5170. (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575. (e) Takeuchi, H.; Fujimoto, T.; Hoshino, K.; Motoyoshiya, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
2. For the syntheses of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Gutierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4336. (b) Moriwake, T.; Hamano, S.; Saito, S.; Torii, S. J. Org. Chem. 1988, 54, 4114. (c) Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1988, 48, 5170. (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575. (e) Takeuchi, H.; Fujimoto, T.; Hoshino, K.; Motoyoshiya, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
3. For the syntheses of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Gutierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4336. (b) Moriwake, T.; Hamano, S.; Saito, S.; Torii, S. J. Org. Chem. 1988, 54, 4114. (c) Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1988, 48, 5170. (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575. (e) Takeuchi, H.; Fujimoto, T.; Hoshino, K.; Motoyoshiya, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
4. For the syntheses of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Gutierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4336. (b) Moriwake, T.; Hamano, S.; Saito, S.; Torii, S. J. Org. Chem. 1988, 54, 4114. (c) Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1988, 48, 5170. (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575. (e) Takeuchi, H.; Fujimoto, T.; Hoshino, K.; Motoyoshiya, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
5. For the syntheses of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Gutierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4336. (b) Moriwake, T.; Hamano, S.; Saito, S.; Torii, S. J. Org. Chem. 1988, 54, 4114. (c) Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1988, 48, 5170. (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575. (e) Takeuchi, H.; Fujimoto, T.; Hoshino, K.; Motoyoshiya, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
6. For examples of the discussion on 1,3-allylic strains in Diels-Alder reactions, see: (a) Crisp, G. T.; Gebauer, M. G. J. Org. Chem. 1996, 61, 8425. (b) Roush, W. R.; Koyama, K.; Curtin, M. L.; Moriarty, K. J. J. Am. Chem. Soc. 1998, 118, 7502. (c) Reetz, M. T.; Kayser, F.; Harms, K. Tetrahedron Lett. 1992, 33, 3453.
7. For examples of the discussion on 1,3-allylic strains in Diels- Alder reactions, see: (a) Crisp, G. T.; Gebauer, M. G. J. Org. Chem. 1996, 61, 8425. (b) Roush, W. R.; Koyama, K.; Curtin, M. L.; Moriarty, K. J. J. Am. Chem. Soc. 1998, 118, 7502. (c) Reetz, M. T.; Kayser, F.; Harms, K. Tetrahedron Lett. 1992, 33, 3453.
8. For examples of the discussion on 1,3-allylic strains in Diels- Alder reactions, see: (a) Crisp, G. T.; Gebauer, M. G. J. Org. Chem. 1996, 61, 8425. (b) Roush, W. R.; Koyama, K.; Curtin, M. L.; Moriarty, K. J. J. Am. Chem. Soc. 1998, 118, 7502. (c) Reetz, M. T.; Kayser, F.; Harms, K. Tetrahedron Lett. 1992, 33, 3453.
9. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676.
10. Supporting Information Table 2.
11. Brown, F. K.; Singh, U. C.; Kollman, P. A.; Raimondi, L.; Houk, K. N.; Bock, C. W. J. Org. Chem. 1992, 57, 4862; Raimondi, L.; Brown, F. K.; Gonzalez, J.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 4796.
12. Brown, F. K.; Singh, U. C.; Kollman, P. A.; Raimondi, L.; Houk, K. N.; Bock, C. W. J. Org. Chem. 1992, 57, 4862; Raimondi, L.; Brown, F. K.; Gonzalez, J.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 4796.
13. Supporting Information Table 3.
14. Atkinson, R. S. Stereoselective Synthesis; John Wiley & Sons: Chichester, 1995; pp 156-180.
15. Supporting Information Tables 2 and 4.
16. Supporting Information Table 4.
17. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: London, 1976.
18. Overman, L. E.; Taylor, G. F.; Houk, K. N.; Domelsmith, L. N. J. Am. Chem. Soc. 1978, 100, 3182.
19. (b) Yedidia, V.; Leznoff, C. C. Can. J. Chem. 1980, 58, 1144.
20. Boeckman, R. K., Jr.; Demko, D. M. J. Org. Chem. 1982, 47, 1789.
21. Spino, C.; Crawford, J.; Cui, Y.; Gugelchuk, M. J. Chem. Soc., Perkin Trans. 2 1998, 1499 and references therein.
22. Supporting Information Table 5.
23. Yoo, X.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 2877. Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183 (Density Functional Theory IV), 1.
24. Yoo, X.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 2877. Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183 (Density Functional Theory IV), 1.
25. Yoo, X.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 2877. Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183 (Density Functional Theory IV), 1.
26. Gaussian 94 and 98: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A.; Gaussian, Inc., Pittsburgh, PA, 1995, 1998.
27. SPARTAN (v. 5.0), Wavefunction, Inc., Irvine, CA.
28. CAChe Scientific, Oxford Molecular, Beaverton, OR.
29. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
30. Szardemings, A. K.; Burkoth, T. S.; Look, G. C.; Campbell, D. A. J. Org. Chem. 1996, 61, 6720.