The stereocontrolled synthesis of enantiopure α-methano heterocycles and constrained amino acid analogs

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 8967-8970

  Hanessian, Stephen ^a   Reinhold, Ulrich ^a   Ninkovic, Sacha ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030577455     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02104-1     Document Type: Article

References (31)

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2. 1. For recent reviews on peptidomimetics see, Peptide Secondary Structure Mimetics. Tetrahedron Symposia-in print No. 50, Kahn, M., Ed., 1993, 49, 2433-3689; Giannis, A.; Kolter, T.; Angew, Chem. Int. Ed. Engl. 1993, 32, 1244; Kahn, M. Synlett 1993, 821.
3. 1. For recent reviews on peptidomimetics see, Peptide Secondary Structure Mimetics. Tetrahedron Symposia-in print No. 50, Kahn, M., Ed., 1993, 49, 2433-3689; Giannis, A.; Kolter, T.; Angew, Chem. Int. Ed. Engl. 1993, 32, 1244; Kahn, M. Synlett 1993, 821.
4. 2. Hanessian, S.; Léger, R. J. Am. Chem. Soc., 1992, 114, 3115; Synlett, 1992, 402.
5. 2. Hanessian, S.; Léger, R. J. Am. Chem. Soc., 1992, 114, 3115; Synlett, 1992, 402.
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7. 3. For recent reviews on free radicals, see: Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron 1990, 46, 1385. Curran, D. P. Synthesis 1988, 417, 489. C-Radicale. In Methoden der Organischen Chemie; Regitz, M.; Giese, B., Eds.; Houben-Weyl: Stuttgart, Germany, 1989; Vol. E19A.
8. 3. For recent reviews on free radicals, see: Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron 1990, 46, 1385. Curran, D. P. Synthesis 1988, 417, 489. C-Radicale. In Methoden der Organischen Chemie; Regitz, M.; Giese, B., Eds.; Houben-Weyl: Stuttgart, Germany, 1989; Vol. E19A.
9. 3. For recent reviews on free radicals, see: Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron 1990, 46, 1385. Curran, D. P. Synthesis 1988, 417, 489. C-Radicale. In Methoden der Organischen Chemie; Regitz, M.; Giese, B., Eds.; Houben-Weyl: Stuttgart, Germany, 1989; Vol. E19A.
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13. 3CN (90% for entry 10). The diastereomers of the Boc-protected lactams (entry 3, 8 and 10) are separable by column chromatography.
14. 7. See for example, Stork, G.; Mah, R. Heterocycles, 1989, 28, 723; Keusenkothen, P. F.; Smith, M. B. Tetrahedron Lett. 1989, 30, 3369; Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536.
15. 7. See for example, Stork, G.; Mah, R. Heterocycles, 1989, 28, 723; Keusenkothen, P. F.; Smith, M. B. Tetrahedron Lett. 1989, 30, 3369; Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536.
16. 7. See for example, Stork, G.; Mah, R. Heterocycles, 1989, 28, 723; Keusenkothen, P. F.; Smith, M. B. Tetrahedron Lett. 1989, 30, 3369; Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536.
17. 8. For carbocyclizations mediated by alkyltin (IV) intermediates, see Macdonald, T. L.; Delahunty, C. M.; Mead, K.; O'Dell, D. E. Tetrahedron Lett. 1989, 30, 1573; Macdonald, T. L.; Mahalingam, S.; O'Dell, D. E. J. Am. Chem. Soc. 1981, 103, 6767; for cyclopropane formation from γ-stannyl alcohols, see Davis, D. D.; Johnson, H. T. J. Am. Chem. Soc. 1974, 96, 7576; Kuivila, H. G.; Scarpa, N. M. J. Am. Chem. Soc. 1970, 92, 6990; for cyclopropane formation from β-stannyl ketones, see Sato, T.; Watanabe, M.; Watanabe, T.; Onoda, Y.; Murayama, E. J. Org. Chem. 1988, 535, 1894; Johnson, C. R., Kadow, J. F. J. Org. Chem. 1987, 52, 1493.
18. 8. For carbocyclizations mediated by alkyltin (IV) intermediates, see Macdonald, T. L.; Delahunty, C. M.; Mead, K.; O'Dell, D. E. Tetrahedron Lett. 1989, 30, 1573; Macdonald, T. L.; Mahalingam, S.; O'Dell, D. E. J. Am. Chem. Soc. 1981, 103, 6767; for cyclopropane formation from γ-stannyl alcohols, see Davis, D. D.; Johnson, H. T. J. Am. Chem. Soc. 1974, 96, 7576; Kuivila, H. G.; Scarpa, N. M. J. Am. Chem. Soc. 1970, 92, 6990; for cyclopropane formation from β-stannyl ketones, see Sato, T.; Watanabe, M.; Watanabe, T.; Onoda, Y.; Murayama, E. J. Org. Chem. 1988, 535, 1894; Johnson, C. R., Kadow, J. F. J. Org. Chem. 1987, 52, 1493.
19. 8. For carbocyclizations mediated by alkyltin (IV) intermediates, see Macdonald, T. L.; Delahunty, C. M.; Mead, K.; O'Dell, D. E. Tetrahedron Lett. 1989, 30, 1573; Macdonald, T. L.; Mahalingam, S.; O'Dell, D. E. J. Am. Chem. Soc. 1981, 103, 6767; for cyclopropane formation from γ-stannyl alcohols, see Davis, D. D.; Johnson, H. T. J. Am. Chem. Soc. 1974, 96, 7576; Kuivila, H. G.; Scarpa, N. M. J. Am. Chem. Soc. 1970, 92, 6990; for cyclopropane formation from β-stannyl ketones, see Sato, T.; Watanabe, M.; Watanabe, T.; Onoda, Y.; Murayama, E. J. Org. Chem. 1988, 535, 1894; Johnson, C. R., Kadow, J. F. J. Org. Chem. 1987, 52, 1493.
20. 8. For carbocyclizations mediated by alkyltin (IV) intermediates, see Macdonald, T. L.; Delahunty, C. M.; Mead, K.; O'Dell, D. E. Tetrahedron Lett. 1989, 30, 1573; Macdonald, T. L.; Mahalingam, S.; O'Dell, D. E. J. Am. Chem. Soc. 1981, 103, 6767; for cyclopropane formation from γ-stannyl alcohols, see Davis, D. D.; Johnson, H. T. J. Am. Chem. Soc. 1974, 96, 7576; Kuivila, H. G.; Scarpa, N. M. J. Am. Chem. Soc. 1970, 92, 6990; for cyclopropane formation from β-stannyl ketones, see Sato, T.; Watanabe, M.; Watanabe, T.; Onoda, Y.; Murayama, E. J. Org. Chem. 1988, 535, 1894; Johnson, C. R., Kadow, J. F. J. Org. Chem. 1987, 52, 1493.
21. 8. For carbocyclizations mediated by alkyltin (IV) intermediates, see Macdonald, T. L.; Delahunty, C. M.; Mead, K.; O'Dell, D. E. Tetrahedron Lett. 1989, 30, 1573; Macdonald, T. L.; Mahalingam, S.; O'Dell, D. E. J. Am. Chem. Soc. 1981, 103, 6767; for cyclopropane formation from γ-stannyl alcohols, see Davis, D. D.; Johnson, H. T. J. Am. Chem. Soc. 1974, 96, 7576; Kuivila, H. G.; Scarpa, N. M. J. Am. Chem. Soc. 1970, 92, 6990; for cyclopropane formation from β-stannyl ketones, see Sato, T.; Watanabe, M.; Watanabe, T.; Onoda, Y.; Murayama, E. J. Org. Chem. 1988, 535, 1894; Johnson, C. R., Kadow, J. F. J. Org. Chem. 1987, 52, 1493.
22. 8. For carbocyclizations mediated by alkyltin (IV) intermediates, see Macdonald, T. L.; Delahunty, C. M.; Mead, K.; O'Dell, D. E. Tetrahedron Lett. 1989, 30, 1573; Macdonald, T. L.; Mahalingam, S.; O'Dell, D. E. J. Am. Chem. Soc. 1981, 103, 6767; for cyclopropane formation from γ-stannyl alcohols, see Davis, D. D.; Johnson, H. T. J. Am. Chem. Soc. 1974, 96, 7576; Kuivila, H. G.; Scarpa, N. M. J. Am. Chem. Soc. 1970, 92, 6990; for cyclopropane formation from β-stannyl ketones, see Sato, T.; Watanabe, M.; Watanabe, T.; Onoda, Y.; Murayama, E. J. Org. Chem. 1988, 535, 1894; Johnson, C. R., Kadow, J. F. J. Org. Chem. 1987, 52, 1493.
23. 9. For Simmons-Smith type cyclopropanations of enol ethers and related compounds, see Hoberg, J. O.; Claffey, D. J. Tetrahedron Lett. 1996, 37, 2533; Timmers, C. M.; Leeuwenburgh, M. A.; Verheijen, J. C.; van der Marel, G. A.; Van Boom, J. H. Tetrahedron: Asymmetry 1996, 7, 49; Boeckman, R. K., Jr.; Charette, A. B.; Asberom, T.; Johnston, B. J. Am. Chem. Soc. 1991, 113, 5227; see also Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Johal, S.; Attwood, M.; Hurst, D. Tetrahedron Lett. 1995, 36, 471.
24. 9. For Simmons-Smith type cyclopropanations of enol ethers and related compounds, see Hoberg, J. O.; Claffey, D. J. Tetrahedron Lett. 1996, 37, 2533; Timmers, C. M.; Leeuwenburgh, M. A.; Verheijen, J. C.; van der Marel, G. A.; Van Boom, J. H. Tetrahedron: Asymmetry 1996, 7, 49; Boeckman, R. K., Jr.; Charette, A. B.; Asberom, T.; Johnston, B. J. Am. Chem. Soc. 1991, 113, 5227; see also Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Johal, S.; Attwood, M.; Hurst, D. Tetrahedron Lett. 1995, 36, 471.
25. 9. For Simmons-Smith type cyclopropanations of enol ethers and related compounds, see Hoberg, J. O.; Claffey, D. J. Tetrahedron Lett. 1996, 37, 2533; Timmers, C. M.; Leeuwenburgh, M. A.; Verheijen, J. C.; van der Marel, G. A.; Van Boom, J. H. Tetrahedron: Asymmetry 1996, 7, 49; Boeckman, R. K., Jr.; Charette, A. B.; Asberom, T.; Johnston, B. J. Am. Chem. Soc. 1991, 113, 5227; see also Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Johal, S.; Attwood, M.; Hurst, D. Tetrahedron Lett. 1995, 36, 471.
26. 9. For Simmons-Smith type cyclopropanations of enol ethers and related compounds, see Hoberg, J. O.; Claffey, D. J. Tetrahedron Lett. 1996, 37, 2533; Timmers, C. M.; Leeuwenburgh, M. A.; Verheijen, J. C.; van der Marel, G. A.; Van Boom, J. H. Tetrahedron: Asymmetry 1996, 7, 49; Boeckman, R. K., Jr.; Charette, A. B.; Asberom, T.; Johnston, B. J. Am. Chem. Soc. 1991, 113, 5227; see also Beddoes, R. L.; Lewis, M. L.; Quayle, P.; Johal, S.; Attwood, M.; Hurst, D. Tetrahedron Lett. 1995, 36, 471.
27. 10. For lactam reduction see Pedregal, C.; Ezquerra, J. Tetrahedron Lett. 1994, 35, 2053. Reduction of lactones was performed by a modified procedure of Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4605.
28. 10. For lactam reduction see Pedregal, C.; Ezquerra, J. Tetrahedron Lett. 1994, 35, 2053. Reduction of lactones was performed by a modified procedure of Bloch, R.; Gilbert, L. J. Org. Chem. 1987, 52, 4605.
29. 11. See for example, Knöpfel, T.; Kuhn, R. Allgeier, H. J. Med. Chem. 1995, 38, 1417; for α-methano benzopyran analogs, see Annoura, H.; Fukunaga, A.; Uesugi, M.; Tatsuoka, T.; Horikawa, Y. Bioorg. Med. Chem. Lett. 1996, 6, 763.
30. 11. See for example, Knöpfel, T.; Kuhn, R. Allgeier, H. J. Med. Chem. 1995, 38, 1417; for α-methano benzopyran analogs, see Annoura, H.; Fukunaga, A.; Uesugi, M.; Tatsuoka, T.; Horikawa, Y. Bioorg. Med. Chem. Lett. 1996, 6, 763.
31. 12. See for example, Chen, X.-Y.; Link, T. M.; Schramm V. L. J. Am. Chem. Soc. 1996, 118, 3067.