Extremely stereoselective alkylation of 3-siloxy-β-lactams and its applications to the asymmetric syntheses of novel 2-alkylisoserines, their dipeptides, and taxoids

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3663-3666

  Ojima, Iwao ^a   Wang, Tao ^a   Delaloge, Francette ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC; DIPEPTIDE; SERINE DERIVATIVE; TAXOID;

ALKYLATION; ARTICLE; CONFORMATIONAL TRANSITION; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION; ENZYME MECHANISM; ENZYME SUBSTRATE; NONHUMAN;

EID: 0032575139     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00643-1     Document Type: Article

References (19)

1. (1) Jung, M. J. In Chemistry and Biochemistry of Amino Acids; G. C. Barret, Ed.; Chapman and Hall: New York, 1985; pp 227-296.
2. (2) e.g., (a) Saari, W. S.; Halczenko, W.; Cochran, D. W.; Dobrinska, M. R.; Vincek, W. C.; Titus, D. G.; Gaul, S. L.; Sweet, C. S. J. Med. Chem., 1984, 27, 713.
3. (b) Saari, W. S.; Freedman, M. B.; Hartman, R. D.; King, S. W.; Raab, A. W.; Randall, W. C.; Engelhardt, E. L.; Hirschmann, R.; Rosegay, A.; Ludden, C. T.; Scriabine, A. J. Med. Chem., 1978, 21, 746.
4. (3) (a) Ramalingam, K.; Woodard, R. W. Tetrahedron Lett., 1985, 26, 1135.
5. (b) Walsh, J. J.; Metzler, D. E.; Powell, D.; Jacobson, R. A. J. Am. Chem. Soc., 1980, 102, 7136.
6. (4) Paul, P. K. C; Sukumar, M.; Bardi, R.; Piazzesi, A. M.; Valle, G.; Toniolo, C.; Balaram, P. J. Am. Chem. Soc., 1986, 108, 6363 and references cited therein.
7. (5) (a) Ojima, I.; Chen, H. J. C.; Qiu, X. Tetrahedron 1988, 44, 5307-5318.
8. (b) Ojima, I.; Komata, T.; Qiu, X. J. Am. Chem. Soc. 1990, 112, 770-774.
9. (6) Ojima, I. In The Organic Chemistry of β-Lactam Antiobiotics; G. I. Georg, Ed.; VCH Publishers: New York, 1992; pp 197-255.
10. (7) Ojima, I. Acc. Chem. Res. 1995, 28, 383-389.
11. (8) Ojima, I.; Park, Y. H.; Sun, C. M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740.
12. (9) Ojima, I.; Sun, C. M.; Park, Y. H. J. Org. Chem. 1994, 59, 1249-1250.
13. (10) Ojima, I.; Duclos, O.; Kuduk, S. D.; Sun, C.-M.; Slater, J. C.; Lavelle, F.; Veith, J. M.; Bernacki, R. J. Bioorg. Med. Chem. Lett. 1994, 4, 2631-2634.
14. (11) Ojima, I.; Slater, J. C.; Michaud, E.; Kuduk, S. D.; Bounaud, P.-Y.; Vrignaud, P.; Bissery, M.-C.; Veith, J.; Pera, P.; Bernacki, R. J. J. Med. Chem. 1996, 39, 3889-3896.
15. (12) Ojima, I.; Slater, J. S.; Kuduk, S. D.; Takeuchi, C. S.; Gimi, R. H.; Sun, C.-M.; Park, Y. H.; Pera, P.; Veith, J. M.; Bernacki, R. J. J. Med. Chem. 1997, 40, 267-278.
16. (13) Ojima, I.; Kuduk, S. D.; Pera, P.; Veith, J. M.; Bernacki, R. J. J. Med. Chem. 1997, 40, 279-285.
17. (14) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y. H.; Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985-7012.
18. (15) Ojima, I.; Ng, E. W.; Sun, C. M. Tetrahedron Letters 1995, 36, 4547-4550.
19. (16) Kant, J.; Schwartz, W. S.; Fairchild, C.; Gao, Q.; Huang, S.; Long, B. H.; Kadow, J. F.; Farina, V.; Vyas, D. Tetrahedron Lett. 1996, 37, 6495-6498.