Stereoselective reduction of α-bromopenicillanates by tributylphosphine

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2889-2892

  Ishiwata, Akihiro ^a   Kotra, Lakshmi P ^a   Miyashita, Kazuyuki ^a   Nagase, Tsuyoshi ^a   Mobashery, Shahriar ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; ESTER; LACTAM; PENICILLANIC ACID; PHOSPHINE DERIVATIVE; TRI N BUTYLPHOSPHINE; TRI-N-BUTYLPHOSPHINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ESTERS; LACTAMS; MODELS, MOLECULAR; OXIDATION-REDUCTION; PENICILLANIC ACID; PHOSPHINES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 0034618316     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000185e     Document Type: Article

References (32)

1. Miyashita, K.; Massova, I.; Taibi, P.; Mobashery, S. J. Am. Chem. Soc. 1995, 117, 11055-11059.
2. Maveyraud, L.; Massova, I.; Birck, C.; Miyashita, K.; Samama, J. P.; Mobashery, S. J. Am. Chem. Soc. 1996, 118, 7435-7440.
3. Mourey, L.; Miyashita, K.; Swarén, P.; Bulychev, A.; Samama, J. P.; Mobashery, S. J. Am. Chem. Soc. 1998, 120, 9383-9385.
4. Golemi, D.; Maveyraud, L.; Vakulenko, S.; Tranier, S.; Ishiwata, A.; Kotra, L. P.; Samama, J. P.; Mobashery, S. J. Am. Chem. Soc. 2000, 122, 6132-6133.
5. Hashizume, T.; Yamaguchi, A.; Hirata, T.; Sawai, T. Antimicrob. Agents Chemother. 1984, 25, 149. Kropp, H.; Gerckens, L.; Sundelof, J. G.; Kahan, F. M. Rev. Inf. Dis. 1985, 7, Suppl 3, S389.
6. Hashizume, T.; Yamaguchi, A.; Hirata, T.; Sawai, T. Antimicrob. Agents Chemother. 1984, 25, 149. Kropp, H.; Gerckens, L.; Sundelof, J. G.; Kahan, F. M. Rev. Inf. Dis. 1985, 7, Suppl 3, S389.
7. Rasmussen, B. A.; Bush, K. Antimicrob. Agents Chemother. 1997, 41, 223-232.
8. Bush, K.; Mobashery, S. How β-Lactamases Have Driven Pharmaceutical Drug Discovery: from Mechanistic Knowledge to Clinical Circumvention. In Resolving the Antibiotic Paradox: Progress in Understanding Drug Resistance and Development of New Antibiotics; Rosen, B. P., Mobashery, S., Eds.; Plenum Press: New York, 1998; pp 71-98.
9. (a) Clayton, J. P. J. Chem. Soc. C 1969, 2123-2127.
10. (b) Sacripante, G.; Just, G. J. Org. Chem. 1987, 52, 3659-3661.
11. For examples, see: (a) Yoshida, A.; Hayashi, T.; Takeda, N.; Oida, S.; Ohki, E. Chem. Pharm. Bull. 1981, 10, 2899-2909.
12. (b) Leanza, W. J.; DiNinno, F.; Muthard, D. A.; Wilening, R. R.; Wildonger, K. J.; Ratcliffe, R. W.; Christensen, B. G. Tetrahedron 1983, 39, 2505-2513.
13. (c) Fujimoto, K.; Iwano, Y.; Hirai, K.; Sugawara, S. Chem. Pharm. Bull. 1986, 34, 999-1014.
14. For examples, see: (a) Ziegler, C. B., Jr.; Fields, T. L. Tetrahedron 1993, 49, 3919-3932.
15. (b) Hanessian, S.; Alpegiani, M. Tetrahedron 1989, 45, 941-950.
16. (c) Foulds, C. D.; Kosmirak, M.; Sammes, P. G. J. Chem. Soc., Perkin. Trans. 1 1985, 963-968.
17. (d) Hirai, K.; Iwano, Y.; Fujimoto, K. Tetrahedron Lett. 1982, 23, 4021-4024.
18. For examples, see: (a) DiNinno, F.; Beattie, T. R.; Christensen, B. G. J. Org. Chem. 1977, 42, 2960-2965.
19. (b) Quallich, G. J.; Bordner, J.; Elliott, M. L.; Morrissey, P.; Volkmann, R. A.; Wroblewska-Adams, M. M. J. Org. Chem. 1990, 55, 367-370.
20. (c) Altamura, M.; Bedeschi, A.; Marchi, M.; Visentin, G.; Francalanci, F. Heterocycles 1991, 32, 1671-1679.
21. For examples, see: (a) Girijavallabhan, V. M.; Ganguly, A. K.; McCombie, S. W.; Pinto, P.; Rizvi, R. Tetrahedron Lett. 1981, 22, 3485-3488.
22. (b) Rossi, R. L.; Kapilani, L. V.; Morrissey, P.; Retsema, J. A. J. Med. Chem. 1990, 33, 291-297.
23. (a) Borowitz, I. J.; Brossman, L. I. Tetrahedron Lett. 1962, 471-474.
24. (b) Borowitz, I. J.; Virkhaus, R. J. Am. Chem. Soc. 1963, 85, 2183-2184.
25. (c) Borowitz, I. J.; Kibby, K. C.; Virkhaus, R. J. Org. Chem. 1966, 42, 4031-4037.
26. Chern, J.-W.; Huang, M.; Tien J-H.; Pai, S.-H. Heterocycles 1988, 27, 1349-1351.
27. 1H NMR of the crude product (α:β = 6.7:1).
28. For examples, see: (a) Durst, T.; LeBelle, M. J. Can. J. Chem. 1972, 50, 3196-3201.
29. (b) Kuhlein, K.; Jensen, H. Liebigs Ann. Chem. 1974, 369-402.
30. (c) Durst, T.; Van Den Elzen, R.; Legault, R. Can. J. Chem. 1974, 52, 3206-3208.
31. (d) Mukerjee, A. K.; Singh, A. K. Synthesis 1975, 547-589.
32. Karn, S. D.; Pau, C. F.; Chamberlin, A. R.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 650-663.