A new access to racemic carbacephems

Bulletin de la Societe Chimique de France

Volumn 133, Issue 10, 1996, Pages 997-1003

  Oumoch, Saïd ^a   Rousseau, Gérard ^a  

^a CNRS   (France)

Author keywords

3 lactam; Azetidinone; Carbacephem; Cyclization; Iminium ion; Lewis acid

Indexed keywords

EID: 0343781059     PISSN: 00378968     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (66)

1. a) Matsukuma I, Yoshiiye S, Mochida K, Hashimoto Y, Saito K, Okachi R, Hirata T, Chem Pharm Bull (1989) 37, 1239
2. b) Blaszczak LC, Brown RF, Cook GK, Hornback WJ, Hoying RC, Indelicato JM, Jordan CL, Katner AS, Kinnick MD, Me Donald III JH, Morin Jr JM, Munroe JE, Pasini CE, J Med Chem (1990) 33, 1656
3. a) Gao C, Chin NX, Neu HC, J Antimicrob Chemother (1988) 22, 155
4. b) Deeter JB, Hall DA, Jordan CL, Justice RM, Kinnick MD, Morin Jr JM, Paschal JW, Ternansky RJ, Tetrahedron Lett (1993) 34. 3051
5. a) Cooper RDG, In: The Chemistry of Beta-Lactams, Page MI, Ed, Blackie and Son, London, 1992, 272-305
6. b) Kant J, Walker DG, In: The Organic Chemistry of BetaLactams, Georg GI, Ed, VCH, New York, 1993, 121-196
7. a) Hegedus LS, Imwinkelried R, Alarid-Sargent M, Dvorak D, Satoh Y, J Am Chem Soc (1990) 112, 1109 and references cited therein
8. b) Burgemeister T, Dannhardt G, Mach-Bindl M, Noeth H, Arch Pharm (1988) 321, 349
9. Burgemeister T, Dannhardt G, Mach-Bindl M, Arch Pharm (1988) 321, 521
10. a) Brunwin DM, Lowe G, Parker J, J Chem Soc, Chem Commun (1971) 865
11. b) Toda F, Tanaka K, Yagi M, Tetrahedron (1987) 43, 1495
12. Mori M, Higuchi Y, Kagechika K, Shibasaki M, Heterocycles (1989) 29, 853
13. Berrien JF, Billion MA, Husson HP, Royer J, J Org Chem (1995) 60, 2922
14. a) Salzmann TN, Ratcliffe RW, Christensen BG, Tetrahedron Lett (1980) 21, 1193
15. b) Barrett AGM, Graboski GG, Russell MA, J Org Chem (1985) 50, 2603
16. Evans DA, Sjogran EB, Tetrahedron Lett (1985) 26, 3787
17. Doyle MP, Shanklin MS, Oon SM, Pho HQ, Van der Heide FR, Veal WR, J Org Chem (1988) 53, 3384
18. e) Joyeau R, Kobaiter R, Sadet J, Wakselman M, Tetrahedron Lett (1989) 30, 337
19. f) Shakya SR, Durst T, Can J Chem (1992) 70, 2142
20. g) Gasparski CM, Ghosh A, Miller MJ, J Org Chem (1992) 57, 3546
21. h) Teng M, Gasparski CM, Williams MA, Miller MJ, Bioorg Med Chem Lett (1993) 3, 2431 and references cited therein 7 C2-C3 bond formation:
22. a) Guthikonda RN, Cama LD, Christensen BG, J Am Chem Soc (1974) 96, 7584
23. b) Uyeo S, Ona H, Chem Pharm Bull (1980) 28, 1563, 1578
24. Foxton MW, Mearman RC, Newall CE, Ward P, Tetrahedron Lett (1981) 22, 2497
25. Bremmer JAS, Colvin EW, Gallacher G, MacLeod A, Tetrahedron Lett (1983) 24, 3783
26. e) Hatanaka M, Ishimaru T, Tetrahedron Lett (1983) 24, 4837
27. f) Herdewijn P, Claes PJ, Vanderhaeghe H, J Med Chem (1986) 29, 661
28. g) Bachi MD, De Mesmaeker A, Stevenart-De Mesmaeker N, Tetrahedron Lett (1987) 28, 2637
29. h) Mochida K, Hirata T, Chem Pharm Bull (1988) 36, 3642
30. Saito H, Matsushima H, Shiraki C, Hirata T, Chem Pharm Bull (1989) 37, 275
31. JW, Gardner JP, Graves BJ, Hines P, Hoying RC, Jackson BG, Kinnick MD, Kochert CD, Lewis JS, Luke WD, Moore LL, Morin JM, Nist RL, Prather DE, Sparks DL, Vladuchick WC, Tetrahedron Lett (1989) 30, 2321
32. k) Saito H, Suzuki F, Hirata T, Chem Pharm Bull (1989) 37, 2298 and references cited therein
33. Jackson BG, Gardner JP, Heath PC, Tetrahedron Lett (1990) 31, 6317
34. Neyer G, Achatz J, Danzer B, Ugi I, Heterocydes (1990) 30, 863
35. n) Frazier JW, Staszak MA, Weigel LO, Tetrahedron Lett (1992) 33, 857
36. o) Dunlap NK, Dezube M, Keith DD, Weigele M, Tetra-hedron Lett (1992) 33, 6103
37. p) Narukawa Y, Juneau KN, Snustad D, Miller DB, Hegedus LS, J Org Chem (1992) 57, 5453
38. q) Saito S, Ishikawa T, Moriwake T, Synlett (1993) 139
39. r) Lotz BT, Miller MJ, J Org Chem (1993) 58, 618
40. s) Ternansky RJ, Jordan CL, Bioorg Med Chem Lett (1993) 3, 2443
41. t) Bosch E, Bachi MD, J Org Chem (1993) 58, 5581
42. u) Guzzo PR, Miller MJ, J Org Chem (1994) 59, 4862
43. Crocker PJ, Miller MJ, J Org Chem (1995) 60, 6176
44. w) Crocker PJ, Karlsson-Andreasson U, Lotz BT, Miller MJ, Heterocydes (1995) 40, 691
45. De Ridder DJA, Goubitz K, Reiss CA, Schenk H, Hiemstra H, Ada Cryst (1996) C52, 1473 C3-C4 bond formation:
46. y) Doyle TW, Conway TT, Casey M, Lim G, Can J Chem (1979) 57, 222
47. z) Knight J, Parsons PJ, J Chem Soc, Perkin Trans I (1987) 1237 C5-C6 bond formation:
48. aa) Kametani T, Honda T, Heterocydes (1982) 19, 1861
49. ab) Beckwith ALJ, Boate DR, Tetrahedron Lett (1985) 26, 1761
50. ac) Kametani T, Chu SD, Itoh A, Maeda S, Honda T, Heterocydes (1988) 27, 875
51. ad) Kametani T, Chu SD, Itoh A, Maeda S, Honda T, J Org Chem (1988) 53, 2683
52. ae) Bachi MD, Bar-Ner N, Bioorg Med Chem Lett (1993) 3, 2439
53. Meyers AI, Sowin TJ, Scholz S, Ueda Y, Tetrahedron Lett (1987) 28, 5103
54. a) Zaugg HE, Synthesis (1984) 85 and 181
55. b) Speckamp WN, Hiemstra H, Tetrahedron (1985) 41, 4371
56. Mickel SJ, Hsiao CN, Miller MJ, Organic Syntheses (1987) 65, 135
57. Kraus GA, Neuenscluvander K, J Chem Soc, Chem Commun (1982) 134
58. Jouglet B, Oumoch S, Rousseau G, Synth Commun (1995) 25, 3869
59. a) Esch PM, Boska IM, Hiemstra H, Speckamp WN, Synlett (1989) 38
60. b) Esch PM, Boska IM, Hiemstra H, De Boer RF, Speckamp WN, Tetrahedron (1991) 47, 4039
61. Haasnoot CAG, de Leeuw FAAM, Altona C, Tetrahedron (1980) 36, 2783
62. Bunnelle WH, Narayanan BA, Organic Syntheses (1990) 69, 89
63. Itoh K, Yogo T, Ishii Y, Chem Lett (1977) 103
64. Xiao YY, Park SK, Prestwich GG, J Org Chem (1988) 53, 4869
65. Homosi A, Hashimoto H, Sakurai H, Tetrahedron Lett (1980) 21, 951
66. Baxter AJG, Dickinson KH, Roberts PM, Smale TC, Southgate R, J Chem Soc, Chem Commun (1979) 236