Total synthesis of the β-adrenergic receptor antagonist, the tetrahydroisoquinoline MY336-a and its epimer

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1996, Pages 2497-2505

  Kaufman, Teodoro S ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748965180     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960002497     Document Type: Article

References (35)

1. H. Kase, H. Fujita, J. Nakamura, K. Hashizumi, J. Goto, K. Kubo and K. Shito, J. Antibiot., 1986, 39, 355.
2. N. Hirayama, T. Iida and K. Shirahata, Acta Crystallogr., Sect. C, 1990, 46, 86.
3. R. P. Williams, H. R. Hill, D. Hawkins, Jr., K.-C. Chao and H. S. Lipscomb, Bacteriological Proceedings of the 66th Annual Meeting of the American Society of Microbiology, California, 1966, Abstract M-159.
4. T. S. Kaufman, Synth. Commun., 1993, 23, 473, and references cited therein.
5. R. M. Williams, P. P. Ehrlich, W. Zhai and J. Hendrix, J. Org. Chem., 1987, 52, 2615.
6. N. Saito, Y. Obara, M. Azumaya and A. Kubo, Chem. Pharm. Bull., 1992, 40, 2620.
7. T. S. Kaufman, J. Chem. Soc., Perkin Trans. 1, 1993, 403.
8. (a) V. L. Ponzo and T. S. Kaufman, Can. J. Chem., 1995, 73, 1348;
9. (b) V. L. Ponzo and T. S. Kaufman, Synlett, 1995, 1149.
10. (a) H. W. Gschwend and H. Rodriguez, Org. React. (N. Y.), 1978, 19, 1;
11. (b) J. A. Gainor and S. M. Weinreb, J. Org. Chem., 1981, 46, 4317.
12. (a) M. Chini, P. Crotti, E. Giovani, F. Macchia and M. Pineschi, Synlett, 1992, 303;
13. (b) A. Solladié-Cavallo and M. Bencheqroun, J. Org. Chem., 1992, 57, 5831.
14. A. García, L. Castedo and D. Domínguez, Synlett, 1993, 271.
15. (a) D. L. Hughes, Org. React. (N.Y.), 1992, 42, 335;
16. (b) D. Papaioannou, C. Athanassopoulos, V. Magafa, N. Karamanos, G. Stavropoulos, A. Napoli, G. Sindona, D. W. Aksnes and G. W. Francis, Acta Chim. Scand., 1994, 48, 324.
17. A. J. Birch, A. H. Jackson and P. V. R. Shannon, J. Chem. Soc., Perkin Trans. 1, 1974, 2185, and references cited therein.
18. J. M. Bobbitt, J. McNew Kiely, K. L. Khana and R. Ebermann, J. Org. Chem., 1965, 30, 2247.
19. J. Barluenga, J. Perez-Prieto and G. Asensio, J. Chem. Soc., Perkin Trans. 1, 1984, 629.
20. C. K. Lau, C. Dufresne, P. C. Bélanger, S. Piétré and J. Scheigetz, J. Org. Chem., 1986, 51, 3038.
21. Y. Yamamoto, T. Nakada and H. Nemoto, J. Am. Chem. Soc., 1992, 114, 121.
22. (a) B. R. de Costa and L. Radesca, Synthesis, 1992, 887;
23. (b) T. Shono, Y. Matsumura, S. Katoh, K. Takeuchi, K. Sasaki, T. Kamada and R. Shimizu, J. Am. Chem. Soc., 1990, 112, 2368.
24. (a) J. Åhman and P. Somfai, Tetrahedron, 1992, 48, 9537;
25. (b) J. Sisko, J. R. Henry and S. M. Weinreb, J. Org. Chem., 1993, 58, 4945.
26. (a) T. Katoh, Y. Nagata, Y. Kobayashi, K. Arai, J. Minami and S. Terashima, Tetrahedron, 1994, 50, 6221;
27. (b) T. Katoh, M. Kirihara, Y. Nagata, Y. Kobayashi, K. Arai, J. Minami and S. Terashima, Tetrahedron, 1994, 50, 6239;
28. (c) C. Agami, F. Couty, M. Poursoulis and J. Vaissermann, Tetrahedron, 1992, 48, 431;
29. (d) R. V. Stevens, Acc. Chem. Res., 1984, 17, 289.
30. C. Ludwig and L.-G. Wistrand, Acta Chim. Scand., 1994, 48, 367.
31. (a) P. A. Grieco, M. Nishizawa, N. Marinovic and W. J. Ehmann, J. Am. Chem. Soc., 1976, 98, 7102;
32. (b) K. Tani, T. Yamagata, S. Akutagawa, H. Kumobayashi, T. Taketomi, H. Takaya, A. Miyashita, R. Noyori and S. Otsuka, J. Am. Chem. Soc., 1984, 106, 5208.
33. V. du Vigneaud and O. K. Behrens, J. Biol. Chem., 1937, 117, 27.
34. G. Bringmann, R. Weirich, H. Reuscher, J. R. Jansen, L. Kinzinger and T. Ortmann, Liebigs Ann. Chem., 1993, 877.
35. H. Kase, personal communication.