Total synthesis of tricyclic β-lactams

Tetrahedron

Volumn 55, Issue 11, 1999, Pages 3427-3443

  Hanessian, Stephen ^a   Reddy, Bhaskar ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINONE DERIVATIVE; CARBAPENEM; FURAN DERIVATIVE; PENEM DERIVATIVE; TRIBACTAM;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033105329     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01152-1     Document Type: Article

References (60)

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32. Hanessian, S.; Couture, C. A.; Georgopapadakou, N. Bioorg. Med. Chem. Lett. 1993, 3, 2323; Sumi, K.; Di Fabio, R.; Hanessian, S. Tetrahedron Lett. 1992, 33, 749; Hanessian, S.; Sumi, K.; Vanasse, B. Synlett 1992, 33; Hanessian, S.; Desilets, D.; Bennani, Y.L. J. Org. Chem. 1990, 55, 3098; Hanessian, S.; Desilets, D. In Trends in Medicinal Chemistry; van der Groot, H.; Domany, G.; Pallos, L.; Timmerman, H. eds.; Elsevier, Amsterdam, 1989, p 165; Hanessian, S.; Alpegiani, M. Tetrahedron, 1989, 45, 941; Hanessian, S.; Bedeschi, A.; Battistini, C.; Mongelli, N. J. Am. Chem. Soc. 1985, 107, 1438.
33. Hanessian, S.; Couture, C. A.; Georgopapadakou, N. Bioorg. Med. Chem. Lett. 1993, 3, 2323; Sumi, K.; Di Fabio, R.; Hanessian, S. Tetrahedron Lett. 1992, 33, 749; Hanessian, S.; Sumi, K.; Vanasse, B. Synlett 1992, 33; Hanessian, S.; Desilets, D.; Bennani, Y.L. J. Org. Chem. 1990, 55, 3098; Hanessian, S.; Desilets, D. In Trends in Medicinal Chemistry; van der Groot, H.; Domany, G.; Pallos, L.; Timmerman, H. eds.; Elsevier, Amsterdam, 1989, p 165; Hanessian, S.; Alpegiani, M. Tetrahedron, 1989, 45, 941; Hanessian, S.; Bedeschi, A.; Battistini, C.; Mongelli, N. J. Am. Chem. Soc. 1985, 107, 1438.
34. Hanessian, S.; Couture, C. A.; Georgopapadakou, N. Bioorg. Med. Chem. Lett. 1993, 3, 2323; Sumi, K.; Di Fabio, R.; Hanessian, S. Tetrahedron Lett. 1992, 33, 749; Hanessian, S.; Sumi, K.; Vanasse, B. Synlett 1992, 33; Hanessian, S.; Desilets, D.; Bennani, Y.L. J. Org. Chem. 1990, 55, 3098; Hanessian, S.; Desilets, D. In Trends in Medicinal Chemistry; van der Groot, H.; Domany, G.; Pallos, L.; Timmerman, H. eds.; Elsevier, Amsterdam, 1989, p 165; Hanessian, S.; Alpegiani, M. Tetrahedron, 1989, 45, 941; Hanessian, S.; Bedeschi, A.; Battistini, C.; Mongelli, N. J. Am. Chem. Soc. 1985, 107, 1438.
35. Hanessian, S.; Reddy, G. B. Bioorg. Chem. Lett. 1993, 3, 2193.
36. Cohen, N. Advan. Drug Res. 1985, 14, 41; J. Med. Chem. 1983, 26, 259.
37. Cohen, N. Advan. Drug Res. 1985, 14, 41; J. Med. Chem. 1983, 26, 259.
38. 4-Acetoxy-3-[(R)-1'-hydroxyethyl]-r-[O-tert-butyldimethylsilyl]-2-azetidin-l-one l, is commercially available, Aldrich Chemical Company Inc., Milwaukee, Wis., and from Kaneka America Corp., New York, N.Y.
39. For the reactions of 2-trimethylsilyloxyfuran with carbonyl compounds, see: Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037; Rassu, G.; Spanu, P.; Casiraghi, G.; Pinna, L. Tetrahedron 1991, 47, 8025 and the references cited therein. For the reactions of 2-trimethylsilyloxyfuran with cyclic imines, see: Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Martin, S. F.; Corbett, J. W. Synthesis 1992, 55 and references cited therein.
40. For the reactions of 2-trimethylsilyloxyfuran with carbonyl compounds, see: Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037; Rassu, G.; Spanu, P.; Casiraghi, G.; Pinna, L. Tetrahedron 1991, 47, 8025 and the references cited therein. For the reactions of 2-trimethylsilyloxyfuran with cyclic imines, see: Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Martin, S. F.; Corbett, J. W. Synthesis 1992, 55 and references cited therein.
41. For the reactions of 2-trimethylsilyloxyfuran with carbonyl compounds, see: Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037; Rassu, G.; Spanu, P.; Casiraghi, G.; Pinna, L. Tetrahedron 1991, 47, 8025 and the references cited therein. For the reactions of 2-trimethylsilyloxyfuran with cyclic imines, see: Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Martin, S. F.; Corbett, J. W. Synthesis 1992, 55 and references cited therein.
42. For the reactions of 2-trimethylsilyloxyfuran with carbonyl compounds, see: Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037; Rassu, G.; Spanu, P.; Casiraghi, G.; Pinna, L. Tetrahedron 1991, 47, 8025 and the references cited therein. For the reactions of 2-trimethylsilyloxyfuran with cyclic imines, see: Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697; Martin, S. F.; Corbett, J. W. Synthesis 1992, 55 and references cited therein.
43. Newton, R. F; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R. and Roberts, S. M. Tetrahedron Lett. 1979, 3981.
44. Shibuya, M.; Kuretani, M; Bukota, S. Tetrahedron 1982, 38, 2659; see also Heinzer, F.; Soukup, M.; Eschenmoser, A. Helv. Chim. Acta 1978, 67, 2851.
45. Shibuya, M.; Kuretani, M; Bukota, S. Tetrahedron 1982, 38, 2659; see also Heinzer, F.; Soukup, M.; Eschenmoser, A. Helv. Chim. Acta 1978, 67, 2851.
46. Shih, D. H.; Baker, F.; Cama, L.; Christensen, B.G. Heterocycles 1984, 21, 29.
47. Compound 12 was prepared from 2. Treatment of 2-trimethylsilyoxyfuran with PhSCI gave 4-phenylthiobutyrolactone, which on treatment with NaHMDS in THF and trapping the enolate with TMS-chloride afforded 12.
48. The stereochemistry was assigned based on nOe studies.
49. For a review on HLE inhibitors, see Edward, P. D.; Bernstein, P. R. Medicinal Research Reviews 1994, 14, 127 and references cited therein. We thank Dr. E. Perrone of Pharmacia/Upjohn for the biological tests.
50. Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137; Grieco, P. A.; Miyashita, M. J. Org. Chem. 1974, 39, 120.
51. Sharpless, K. B.; Lauer, R. F.; Teranishi, A. Y. J. Am. Chem. Soc. 1973, 95, 6137; Grieco, P. A.; Miyashita, M. J. Org. Chem. 1974, 39, 120.
52. Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979, 35, 2169; Arnarp, J.; Onngren, J. Acta Chem. Scand. Ser B, 1978, 32, 465; Greene, A. E.; Drian, C. L.; Crabble, P. J. Am. Chem. Soc. 1980, 102, 7583; Reuvers, J. T. A.; De Groot, A. J. Org. Chem. 1986, 51, 4594; Jung, M. E.; Kaas, S. M. Tetrahedron Lett. 1989, 30, 641.
53. Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979, 35, 2169; Arnarp, J.; Onngren, J. Acta Chem. Scand. Ser B, 1978, 32, 465; Greene, A. E.; Drian, C. L.; Crabble, P. J. Am. Chem. Soc. 1980, 102, 7583; Reuvers, J. T. A.; De Groot, A. J. Org. Chem. 1986, 51, 4594; Jung, M. E.; Kaas, S. M. Tetrahedron Lett. 1989, 30, 641.
54. Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979, 35, 2169; Arnarp, J.; Onngren, J. Acta Chem. Scand. Ser B, 1978, 32, 465; Greene, A. E.; Drian, C. L.; Crabble, P. J. Am. Chem. Soc. 1980, 102, 7583; Reuvers, J. T. A.; De Groot, A. J. Org. Chem. 1986, 51, 4594; Jung, M. E.; Kaas, S. M. Tetrahedron Lett. 1989, 30, 641.
55. Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979, 35, 2169; Arnarp, J.; Onngren, J. Acta Chem. Scand. Ser B, 1978, 32, 465; Greene, A. E.; Drian, C. L.; Crabble, P. J. Am. Chem. Soc. 1980, 102, 7583; Reuvers, J. T. A.; De Groot, A. J. Org. Chem. 1986, 51, 4594; Jung, M. E.; Kaas, S. M. Tetrahedron Lett. 1989, 30, 641.
56. Johnstone, R. A. W.; Rose, M. E. Tetrahedron 1979, 35, 2169; Arnarp, J.; Onngren, J. Acta Chem. Scand. Ser B, 1978, 32, 465; Greene, A. E.; Drian, C. L.; Crabble, P. J. Am. Chem. Soc. 1980, 102, 7583; Reuvers, J. T. A.; De Groot, A. J. Org. Chem. 1986, 51, 4594; Jung, M. E.; Kaas, S. M. Tetrahedron Lett. 1989, 30, 641.
57. Direct reduction of anomeric hydroxyl group to give tetrahydrofuran motif was not successful.
58. See for example Hanessian, S.; Desilets, D.; Bennani, Y. J. Org. Chem. 1990, 55, 3098.
59. According to Autonom (Beilstein), this compound can be named as "2-[1-tert-butyl-dimethylsilanyloxy)ethyl]-2b-methyl-1,4-dioxo-octahydro-3-oxa-6a-aza-cyclobuta[a]pentalene-6-carboxylic acid benzyl ester".
60. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem., 1978, 43, 2923.