Enantiospecific synthesis of γ-keto-α,β-diamino acid derivatives. Stereoselective synthesis of a precursor of streptolidine lactam

Tetrahedron Letters

Volumn 38, Issue 4, 1997, Pages 673-676

  Fernández Megía, Eduardo ^a   Sardina, F Javier ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; LACTAM DERIVATIVE; STREPTOTHRICIN;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; STEREOISOMERISM;

EID: 0343907301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02389-1     Document Type: Article

References (34)

1. Carter, H. E.; Clark, R. K. Jr.; Kohn, P.; Rothrock, J. W.; Taylor, W. R.; West, C. A.; Whitfield, G. B.; Jackson, W. G. J. Am. Chem. Soc. 1954, 76, 566-569.
2. Nakanishi, K.; Ito, T.; Hirata, Y. J. Am. Chem. Soc. 1954, 76, 2845-2846.
3. Brockmann, H.; Musso, H. Chem. Ber. 1955, 88, 648-661.
4. (a) Borders, D. B.; Hausmann, W. K.; Wetzel, E. R.; Patterson, E. L. Tetrahedron Lett. 1967, 4187-4192.
5. (b) Borders, D. B.; Sax, K. J.; Lancaster, J. E.; Hausmann, W. K.; Mitscher, L. A.; Wetzel, E. R.; Patterson, E. L. Tetrahedron 1970, 26, 3123-3133.
6. (c) Kawakami, Y.; Yamasaki, K.; Nakamura, S. J. Antibiotics 1981, 34, 921-922.
7. Kido, Y.; Furuie, T.; Suzuki, K.; Sakamoto, K.; Yokoyama, Y.; Uyeda, M.; Kinjyo, J.; Yahara, S.; Nohara, T.; Shibata, M. J. Antibiotics 1987, 40, 1698-1706.
8. (a) Goto, T.; Ohgi, T. Tetrahedron Lett. 1974, 1413-1416.
9. (b) Kusumoto, S.; Tsuji, S.; Shiba, T. Tetrahedron Lett. 1974, 1417-1420.
10. (c) Kusumoto, S.; Tsuji, S.; Shiba, T. Bull. Chem. Soc. Jpn. 1974, 47, 2690-2695.
11. (d) Kusumoto, S.; Tsuji, S.; Shima, K.; Shiba, T. Bull. Chem. Soc. Jpn. 1976, 49, 3611-3614.
12. Kinoshita, M.; Suzuki, Y. Bull. Chem. Soc. Jpn. 1977, 50, 2375-2378.
13. Kusumoto, S.; Imaoka, S.; Kambayashi, Y.; Shiba, T. Tetrahedron Lett. 1982, 23, 2961-2964.
14. Fernandez-Megía, E.; Paz, M. M.; Sardina, F. J. J. Org. Chem. 1994, 59, 7643-7652.
15. Yamazaki, N.; Kibayashi, C. J. Am. Chem. Soc. 1989, 111, 1396-1408.
16. 2).
17. 2. 4a and 4c-e were purified by column chromatography on silicagel. Crude 4b was used directly in the next step due to its instability towards silicagel.
18. 16g-h
19. 1-Ethoxy-1-lithioethene was prepared from ethyl vinyl ether (300 mol%) and tBuLi (250 mol%) (THF, -78 °C). This solution was allowed to reach 0 °C and was stirred at 0°C for 45 min, then it was cooled to -78 °C, and cannulated into a solution of 3 (THF, -78 °C). The reaction was allowed to reach -55 °C and then was stirred at this temperature for 45 min prior to quench. (a) Angelastro, M. R.; Peet, N. P.; Bey, P. J. Org. Chem. 1989, 54, 3913-3916.
20. (b) Soderquist, J. A.; Hsu, G. J.-H. Organometallics 1982, 1, 830-833.
21. O'Neill, B. T. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 398-399.
22. For methods to convert carboxylic acid derivatives into ketones see: (a) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
23. (b) Masamune, S.; Choy, W.; Kerdesky, F. A. J.; Imperiali, B. J. Am. Chem. Soc. 1981, 103, 1566-1568.
24. (c) Rubottom, G. M.; Kim, C. J. Org. Chem. 1983, 48, 1550-1552.
25. (d) Buckley, T. F. III; Rapoport, H. J. Am. Chem. Soc. 1981, 103, 6157-6163.
26. (e) Knudsen, C. G.; Rapoport, H. J. Org. Chem. 1983, 48, 2260-2266.
27. (f) Creary, X. J. Org. Chem. 1987, 52, 5026-5030.
28. (g) Barluenga, J.; Llavona, L.; Concellón, J. M.; Yus, M. J. Chem. Soc., Perkin Trans. 1 1991, 297-300.
29. (h) Barluenga, J.; Baragaña, B.; Concellón, J. M. J. Org. Chem. 1995, 60, 6696-6699, and references therein.
30. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370-2374.
31. (a) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205.
32. (b) Brady, S. F.; Varga, S. L.; Freidinger, R. M.; Schwenk, D. A.; Mendlowski, M.; Holly, F. W.; Veber, D. F. J. Org. Chem. 1979, 44, 3101-3105.
33. (c) Brady, S. F.; Freidinger, R. M.; Paleveda, W. J.; Colton, C. D.; Homnick, C. F.; Whitter, W. L.; Curley, P.; Nutt, R. F.; Veber, D. F. J. Org. Chem. 1987, 52, 764-769.
34. Dunn, P. J.; Häner, R.; Rapoport, H. J. Org. Chem. 1990, 55, 5017-5025.