Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels-Alder reaction

Tetrahedron Letters

Volumn 43, Issue 41, 2002, Pages 7389-7392

  Murray, William V ^a   Mishra, Pranab K ^a   Sun, Sengen ^a   Maden, Amy ^a  

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

Author keywords

Intramolecular hetero Diels Alder reaction; Pyrrolidinone; Remote hydroxylation

Indexed keywords

CHEMICAL COMPOUND; PYRROLIDINONE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; HYDROXYLATION; MOLECULAR MECHANICS; STEREOCHEMISTRY; SYNTHESIS;

BETULACEAE;

EID: 0037037838     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01711-2     Document Type: Article

References (22)

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6. For synthesis of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Guitierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4335; (b) Moriwake, T.; Hmano, S.; Saito, S.; Torii, S.; J. Org. Chem. 1989, 54, 4114; © Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170; (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575; (e) Takeuchi, H.; Fujimoto, T.; Hshino, K.; Motoyoshia, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
7. For synthesis of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Guitierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4335; (b) Moriwake, T.; Hmano, S.; Saito, S.; Torii, S.; J. Org. Chem. 1989, 54, 4114; © Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170; (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575; (e) Takeuchi, H.; Fujimoto, T.; Hshino, K.; Motoyoshia, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
8. For synthesis of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Guitierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4335; (b) Moriwake, T.; Hmano, S.; Saito, S.; Torii, S.; J. Org. Chem. 1989, 54, 4114; © Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170; (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575; (e) Takeuchi, H.; Fujimoto, T.; Hshino, K.; Motoyoshia, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
9. For synthesis of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Guitierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4335; (b) Moriwake, T.; Hmano, S.; Saito, S.; Torii, S.; J. Org. Chem. 1989, 54, 4114; © Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170; (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575; (e) Takeuchi, H.; Fujimoto, T.; Hshino, K.; Motoyoshia, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
10. For synthesis of other hydroisoquinone and hydroisoindole derivatives via Diels-Alder reactions, see: (a) Guitierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4335; (b) Moriwake, T.; Hmano, S.; Saito, S.; Torii, S.; J. Org. Chem. 1989, 54, 4114; © Martin, S.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170; (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P. Tetrahedron Lett. 1985, 26, 3575; (e) Takeuchi, H.; Fujimoto, T.; Hshino, K.; Motoyoshia, J.; Kakehi, A.; Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
11. For synthesis of 6,5 fused systems via oxo Diels-Alder reactions, see: Tietze, L. F.; Beifuss, U.; Ruthe, M.; Ruhlmann, A.; Antel, J.; Sheldrick, G. M. Angew. Chem., Int. Ed. 1988, 27, 1186-1187; Tietze, L. F.; Bachmann, J.; Scul, W. Angew. Chem., Int. Ed. 1988. 27, 971-973.
12. For synthesis of 6,5 fused systems via oxo Diels-Alder reactions, see: Tietze, L. F.; Beifuss, U.; Ruthe, M.; Ruhlmann, A.; Antel, J.; Sheldrick, G. M. Angew. Chem., Int. Ed. 1988, 27, 1186-1187; Tietze, L. F.; Bachmann, J.; Scul, W. Angew. Chem., Int. Ed. 1988. 27, 971-973.
13. Murray W.V., Sun S., Turchi I.J., Brown F.K., Gauthier A.D. J. Org. Chem. 64:1999;5930.
14. Sun S., Turchi I.J., Murray W.V. J. Org. Chem. 65:2000;2555.
15. Sun S., Murray W.V. J. Org. Chem. 64:1999;5941.
16. Synthesis of amino aldehydes and their stability, see: (a) Myers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359-1362; (b) Myers, A. G.; Kung, D. W.; Zhong, B. J. Am. Chem. Soc. 2000, 122, 3226. J. Chem. Soc., Chem. Commun. 1993, 18 1463-1464 and Chem. Lett. 1990, 11, 2043-2046.
17. Synthesis of amino aldehydes and their stability, see: (a) Myers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359-1362; (b) Myers, A. G.; Kung, D. W.; Zhong, B. J. Am. Chem. Soc. 2000, 122, 3226. J. Chem. Soc., Chem. Commun. 1993, 18 1463-1464 and Chem. Lett. 1990, 11, 2043-2046.
18. Synthesis of amino aldehydes and their stability, see: (a) Myers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359-1362; (b) Myers, A. G.; Kung, D. W.; Zhong, B. J. Am. Chem. Soc. 2000, 122, 3226. J. Chem. Soc., Chem. Commun. 1993, 18 1463-1464 and Chem. Lett. 1990, 11, 2043-2046.
19. Synthesis of amino aldehydes and their stability, see: (a) Myers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.; Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41, 1359-1362; (b) Myers, A. G.; Kung, D. W.; Zhong, B. J. Am. Chem. Soc. 2000, 122, 3226. J. Chem. Soc., Chem. Commun. 1993, 18 1463-1464 and Chem. Lett. 1990, 11, 2043-2046.
20. Compounds 4a-c were compared to identical compounds from racemic aldehyde and no racemization was detected by chiral HPLC.
21. While protons on C-5 and C-6 were resolved they were too close to accurately observe NOEs between them.
22. By chiral HPLC.