An efficient synthesis of enantiomerically pure 3-hydroxy-β-lactams via zinc induced removal of a chiral auxiliary

Tetrahedron Asymmetry

Volumn 11, Issue 7, 2000, Pages 1477-1485

  Joshi, Sudhir N ^a   Deshmukh, A R A S ^a   Bhawal, B M ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0034027434     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00098-7     Document Type: Article

References (33)

1. (a) Nagahara, T.; Kamitani, T. Heterocycles 1987, 25, 729.
2. (b) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukac, G.; Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; p. 553.
3. (c) Palomo, C. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukac, G.; Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; p. 565.
4. (d) Van der Steen, F. H.; Van Koten, G. Tetrahedron 1991, 47, 7503.
5. (e) Durckheimer, W.; Blumbach, J.; Latrell, R.; Sheunemann, K. H. Angew. Chem., Int. Ed. Engl. 1985, 24, 180.
6. (a) Manhas, M. S.; Amin, S. G.; Bose, A. K. Heterocycles 1976, 5, 699.
7. (b) Ojima, I. In The Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p. 197.
8. (c) Ojima, I. Acc. Chem. Res. 1995, 28, 383.
9. Ojima, I.; Habus, I.; Zhao, M.; Georg, G. I.; Jayasinghe, L. R. J. Org. Chem. 1991, 56, 1681.
10. Georg, G. I.; Harriman, G. C. B.; Hepperle, M.; Clowers, J. S.; Van der Velde, D. G.; Himes, R. H. J. Org. Chem. 1996, 61, 2664 and references cited therein.
11. (a) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985.
12. (b) Georg, G. I.; Cheruvallath, Z. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. Bioorg. Med. Chem. Lett. 1993, 3, 2467.
13. (c) Ojima, I.; Zucco, M.; Duclos, O.; Kuduk, S. D.; Sun, C. M.; Park, Y. H. Bioorg. Med. Chem. Lett. 1993, 3, 2479.
14. (a) Manhas, M. S.; Amin, S. G.; Chawla, H. P. S.; Bose, A. K. J. Heterocycl. Chem. 1978, 15, 601.
15. (b) Nagao, Y.; Kumageri, T.; Takao, S.; Abe, T.; Ochiai, M.; Inoue, Y.; Taga, T.; Fujita, E. J. Org. Chem. 1986, 51, 4737.
16. (c) Wagle, D. R.; Garai, C.; Chiang, J.; Montleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227.
17. (d) Palomo, C.; Cossio, P. P.; Cuevas, C. Tetrahedron Lett. 1991, 32, 3109.
18. (e) Borer, B. C.; Balogh, D. W. Tetrahedron Lett. 1991, 32, 1039.
19. (a) Holton, R. A.; Liu, J. A. Bioorg. Med. Chem. Lett. 1993, 11, 2475.
20. (b) Palomo, C.; Arrieta, A.; Cossio, P. P.; Aizpura, J. M.; Mielgo, A. I.; Aurrekoetxea, N. Tetrahedron Lett. 1990, 31, 6425, 6429.
21. (a) Basak, A.; Mahato, T.; Bhattaacharya, G.; Mukherjee, B. Tetrahedron Lett. 1997, 38, 643.
22. (b) Brieva, R.; Crish, J. Z.; Sih, C. J. J. Org. Chem. 1993, 58, 1068.
23. (a) Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. Synlett 1992, 749.
24. (b) Jayaraman, M.; Nandi, M.; Sathe, K. M.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron: Asymmetry 1993, 4, 609.
25. (c) Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 932.
26. (d) Jayaraman, M.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron 1996, 52, 3741.
27. (e) Srirajan, V.; Puranik, V. G.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron 1996, 52, 5579.
28. (f) Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron 1996, 52, 5585.
29. (g) Jayaraman, M.; Puranik, V. G.; Bhawal, B. M. Tetrahedron 1996, 52, 9005.
30. (h) Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron 1996, 52, 8989.
31. (i) Srirajan, V.; Deshmukh, A. R. A. S.; Puranik, V. G.; Bhawal, B. M. Tetrahedron: Asymmetry 1996, 7, 2733.
32. Boguslavskaya, L. S. Russ. Chem. Rev. 1972, 41, 740.
33. Dykstra, H. B.; Lewis, J. F.; Boord, C. E. J. Am. Chem. Soc. 1930, 52, 651, 3396.