An Efficient Synthesis of cis-3-Hydroxy-4-phenyl-β-Lactams : Precursor for Taxol Side Chain

Tetrahedron

Volumn 52, Issue 15, 1996, Pages 5585-5590

  Srirajan, V ^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; TAXANE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029965801     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00200-1     Document Type: Article

References (31)

1. a) Ojima, I.; Habus, I.; Zhao, M.; Georg, G.I.; Jayashinge, L.R. J. Org. Chem. 1991, 56, 1681.
2. b) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y.H.; Sun, C.M.; Briguard, T. Tetrahedron 1992, 48, 6985.
3. a) Holmes, F. A.; Walters, R. S.; Theriault, R. L.; Forman, A. D.; Newton, L. K.; Raber, M. N.; Buzdar, A. U.; Frye, D. K.; Hortobagyi, G. N. J. Natl. Cancer Inst. 1991, 83, 1797.
4. b) Rowinsky, E. K.; Casenave, L. A.; Donehower, R. C.; J. Natl. Cancer. Inst. 1990, 82, 1247.
5. c) Blume, E. J. Natl. Cancer. Inst. 1989, 81, 1122.
6. a) Brieva, R.; Crich, J. Z.; Sih, C. J. J. Org. Chem. 1993, 58, 1068.
7. Denis, J.-N.; Greene, A. E.; Gueritte-Voegelein, F.; Mangatal, L.; Potier, P. J. Am. Chem. Soc. 1988, 110, 5917.
8. a) For review see a) Kingston, D.G.I. Pharm. Ther. 1991, 52, 1.
9. b) Senilh, V.; Gueritte, F.; Guenard, D.; Colin, M.; Potier, P. C. Acad. Sci. Paris. 1984. t. 299, Serie II, no. 15, 1039.
10. c) Gueritte-Voegelein, F.; Senilh, V.; David, B.; Guenard, D.; Potier, P. Tetrahedron 1986, 42, 4451.
11. d) Wender, P. A.; Macciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878.
12. Parness, J.; Kingston, D.G.I.; Powell, R.G.; Harracksingh, S.B. Biochem. Biophys. Res. Commun. 1982, 105, 1082.
13. a) Gueritte-Voegelein, F.; Guenard, D.; Mangatal, L.; Potier, P.; Guilhem, J.; Cesario, M.; Pascard, C. Acta. Cryst. 1990, C46, 781.
14. b) Swindell, C. S.; Krauss, N. E.; Horwitz, S. B.; Ringel, I. J. Med. Chem. 1991, 34, 1176.
15. c) Kant, J.; Huang, S.; Wong, H.; Fairchild, C.; Vyas, D.; Farina, V. Bioorg. Med. Chem. Lett. 1993, 3, 2471.
16. d) Georg, G. I.; Cheruvallath, Z. S.; Himes, R. H.; Mejillano, M. R.; Burke, C. T.; J. Med. Chem. 1992, 35, 4230.
17. a) Holton, R. A.; Liu, J. H. Bioorganic & Medicinal Chem. Lett. 1993, 3, 2475.
18. b) Denis, J.-N.; Green, A.E.; Gueritte-Voegelein, F.;Mangatal, L.; Potier, P. J. Am. Chem. Soc. 1988, 110, 5917.
19. Georg, G. I.; Cheruvallath, Z. S.; Harriman, G. C. B.; Hepperie, M.; Park, H. Bioorg. Med. Chem. Lett. 1993, 3, 2467.
20. a) Staudinger, M. Liebigs. Ann. Chem. 1907, 356, 51. Review on chiral control of the Staudinger reaction see:
21. b) Cooper, R. D. G.; Daughery, B. W.; Boyd, D. B. Pure Appl. Chem. 1987, 59, 485.
22. c) Georg, G. I.; Ravikumar, V. T. In The Chemistry of β-lactams; G. I. Georg, Ed.; VCH. New York, 1993, p 295.
23. (a) Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. Synlett, 1992, 9, 749.
24. b) Jayaraman, M.; Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron (in press)
25. Srirajan, V.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron (accepted for publication).
26. For our previous work on use of other chiral auxiliaries see (a) Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. Tetrahedron Asymmetry 1993, 4, 609.
27. b) Jayaraman, M.; Deshmukh, A. R. A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 932.
28. 25D : +12.0 (neat)}
29. Bach, R.D.; Klein, M.W.; Ryntz, R.A.; Holbuka, J.W. J. Org. Chem. 1979, 44, 2569.
30. a) Arlt, D.; Jautelat, M.; Lantzsch, R. Angew. Chem. Int. Ed. Engl. 1981, 20, 703.
31. b) Bhat, N. G.; Joshi, G. D.; Gore, K. G.; Kulkarni, G. H.; Mitra, R. B. Indian J. Chem. 1981, 20B, 558.