Synthetic studies of carzinophilin. Part 1: Synthesis of 2-methylidene-1-azabicyclo[3.1.0]hexane systems related to carzinophilin

Tetrahedron

Volumn 59, Issue 17, 2003, Pages 3019-3040

  Hashimoto, Masaru ^a,b   Matsumoto, Miyoko ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b HIROSAKI UNIVERSITY   (Japan)

Author keywords

Bisalkylating agent; Carzinophilin; Malonylidenes

Indexed keywords

ACETIC ACID DERIVATIVE; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; AZIRIDINE; BICYCLO COMPOUND; CARZINOPHILIN; CHEMICAL COMPOUND; HEXANE; NITRO DERIVATIVE; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; PRIORITY JOURNAL;

EID: 0037459891     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00377-6     Document Type: Article

References (59)

1. Parts of this series of papers have been the subject of five preliminary communications: (a) Hashimoto M., Yamada K., Terashima S. Chem. Lett. 1992;975 (b) Hashimoto M., Matsumoto M., Yamada K., Terashima S. Tetrahedron Lett. 35:1994;2207 (c) Hashimoto M., Terashima S. Chem. Lett. 1994;1001 (d) Hashimoto M., Terashima S. Tetrahedron Lett. 35:1994;9409 (e) Hashimoto M., Terashima S. Heterocycles. 47:1998;59.
2. Parts of this series of papers have been the subject of five preliminary communications: (a) Hashimoto M., Yamada K., Terashima S. Chem. Lett. 1992;975 (b) Hashimoto M., Matsumoto M., Yamada K., Terashima S. Tetrahedron Lett. 35:1994;2207 (c) Hashimoto M., Terashima S. Chem. Lett. 1994;1001 (d) Hashimoto M., Terashima S. Tetrahedron Lett. 35:1994;9409 (e) Hashimoto M., Terashima S. Heterocycles. 47:1998;59.
3. Parts of this series of papers have been the subject of five preliminary communications: (a) Hashimoto M., Yamada K., Terashima S. Chem. Lett. 1992;975 (b) Hashimoto M., Matsumoto M., Yamada K., Terashima S. Tetrahedron Lett. 35:1994;2207 (c) Hashimoto M., Terashima S. Chem. Lett. 1994;1001 (d) Hashimoto M., Terashima S. Tetrahedron Lett. 35:1994;9409 (e) Hashimoto M., Terashima S. Heterocycles. 47:1998;59.
4. Parts of this series of papers have been the subject of five preliminary communications: (a) Hashimoto M., Yamada K., Terashima S. Chem. Lett. 1992;975 (b) Hashimoto M., Matsumoto M., Yamada K., Terashima S. Tetrahedron Lett. 35:1994;2207 (c) Hashimoto M., Terashima S. Chem. Lett. 1994;1001 (d) Hashimoto M., Terashima S. Tetrahedron Lett. 35:1994;9409 (e) Hashimoto M., Terashima S. Heterocycles. 47:1998;59.
5. Parts of this series of papers have been the subject of five preliminary communications: (a) Hashimoto M., Yamada K., Terashima S. Chem. Lett. 1992;975 (b) Hashimoto M., Matsumoto M., Yamada K., Terashima S. Tetrahedron Lett. 35:1994;2207 (c) Hashimoto M., Terashima S. Chem. Lett. 1994;1001 (d) Hashimoto M., Terashima S. Tetrahedron Lett. 35:1994;9409 (e) Hashimoto M., Terashima S. Heterocycles. 47:1998;59.
6. For preliminary communications, see Ref. 1a,b.
7. Hata T., Koga F., Sano Y., Kanamori K., Matsumae A., Sunagawa R., Hoshi T., Shima T., Ito S., Tomizawa S. Antibiot. Ser. A. 7:1954;107.
8. Terawaki A., Greenberg J. Nature. 209:1966;481.
9. Armstrong R.W., Salavati M.E., Nguyen M. J. Am. Chem. Soc. 1992;114.
10. Alcaro S., Coleman R.S. J. Med. Chem. 43:2000;2783.
11. Lown J.W., Hanstock C.C. J. Am. Chem. Soc. 104:1982;3213.
12. Onda M., Konda Y., Hatano A., Hata T., Omura S. J. Am. Chem. Soc. 105:1983;6311.
13. Moran E.J., Armstrong R.W. Tetrahedron Lett. 32:1991;3807.
14. Nagaoka K., Matsumoto M., Oono J., Yokoi K., Ishizeki S., Nakashima T.J. J. Antibiot. 39:1986;1527.
15. Yokoi K., Nagaoka K., Nakashima T. Chem. Phram. Bull. 34:1986;4554.
16. Coleman R.S., Carpenter A.J. J. Org. Chem. 57:1992;5813.
17. Coleman R.S., Carpenter A.J. Tetrahedron Lett. 33:1992;1697.
18. Coleman R.S., Carpenter A.J. J. Org. Chem. 58:1993;4452.
19. Coleman R.S., Carpenter A.J. Tetrahedron. 53:1997;16313.
20. Coleman R.S. Synlett. 1998;1031.
21. Coleman R.S., Kong J.-S., Richardson T.E. J. Am. Chem. Soc. 121:1999;9088.
22. Coleman R.S., Kong J.-S. J. Am. Chem. Soc. 120:1998;3538.
23. Coleman R.S., Li J., Navarro A. Angew. Chem. Int. Ed. 40:2001;1736.
24. Hodgkinson T.J., Shipman M. Tetrahedron. 57:2001;4467.
25. Armstrong R.W., Moran E.J. J. Am. Chem. Soc. 114:1992;371.
26. Armstrong R.W., Tellew J.E., Moran E.J. J. Org. Chem. 57:1992;2208.
27. Armstrong R.W., Tellew J.E., Moran E.J. J. Org. Chem. 58:1993;7848.
28. Bryant H.J., Dardonville C.Y., Hodgkinson T.J., Shipman M., Slawin A.M.Z. Synlett. 1996;973.
29. England P., Chun K.H., Moran E.J., Armstrong R.W. Tetrahedron Lett. 31:1990;2669.
30. Konda Y., Machida T., Akaiwa M., Takeda K., Harigaya Y. Heterocycles. 43:1996;555.
31. Konda Y., Machida T., Sasaki T., Takeda K., Takayanagi H., Harigaya Y. Chem. Phram. Bull. 42:1994;285.
32. Shishido, K.; Omodani, T.; Shibuya, M. Presented at the 113th Annual Meeting of the Pharmaceutical Society of Japan, 1993; Abstract Paper II, p 13.
33. Shishido, K.; Omodani, T.; Shibuya, M. Presented at the 112th Annual Meeting of the Pharmaceutical Society of Japan, 1992; Abstract Paper II, p 135.
34. Shishido K., Omodani T., Shibuya M. J. Chem. Soc. Perkin Trans. 1. 1992;2053.
35. Ando K., Yamada T., Shibuya M. Heterocycles. 29:1989;2209.
36. Shibuya M., Terauchi H. Tetrahedron Lett. 28:1987;2619.
37. Shibuya M. Tetrahedron Lett. 24:1983;1175.
38. Bryant H.J., Dardonville C.Y., Hodgkinson T.J., Shipman M., Slawin A.M.Z. Synlett. 1996;973-974. Synlett 1996, 973.
39. Bryant H.J., Dardonville C.Y., Hodgkinson T.J., Husrthouse M.B., Malik K.M.A., Shipman M. J. Chem. Soc. Perkin Trans. 1. 1998;1249.
40. Hodgkinson T.J., Kelland L.R., Shipman M., Vile J. Tetrahedron. 54:1998;6029.
41. Hodgkinson T.J., Kelland L.R., Shipman M., Suzenet F. Bioorg. Med. Chem. Lett. 10:2000;239.
42. Hartley J.A., Hazrati A., Kelland L.R., Khanim R., Shipman M., Suzenet F., Walker L.F. Angew. Chem. Int. Ed. 39:2000;3467.
43. Uemura I., Yamada K., Sugiura K., Miyagawa H., Ueno T. Tetrahedron: Asymmetry. 12:2001;943.
44. Saijo S., Wada M., Himizu J., Ishida A. Chem. Pharm. Bull. 28:1980;1149.
45. Woo K.-C., Jones K. Tetrahedron Lett. 32:1991;6949.
46. Roth M., Dubs P., Gotschi E., Eschemmoser A. Helv. Chim. Acta. 54:1971;710.
47. Pedersen B.S., Lawesson S.-O. Tetrahedron. 35:1979;2433.
48. Mitsunobu O. Synthesis. 1981;1.
49. Herdeis C., Syvari. J. Arch. Pharm. (Weinheim). 321:1988;491.
50. Wick A.E., Bartlett P.A., Dolphin D. Helv. Chim. Acta. 54:1971;513.
51. Sato, H. T. S.; Hirama, M. Presented at the 59th Annual Meeting of the Chemical Society of Japan, 1990; Abstract Paper II, p 1124.
52. Bodanszky M., Bodanszky A. Practice of Peptide Synthesis. 1994;Springer, Heidelberg.
53. Celerier J.P., D-Marchalant E., Lhommet G. J. Heterocycl. Chem. 21:1984;1633.
54. Brunerie P., Celerier J.P., Petit H., Lhommet G. J. Heterocycl. Chem. 23:1986;1183.
55. PC Spartan Pro Ver. 1.08 (Wavefunction Inc.) was employed for calculations.
56. Hariharan P.C., Pople J.A. Chem. Phys. Lett. 66:1972;217.
57. Allinger N.L. J. Am. Chem. Soc. 99:1977;8127.
58. Dewar M.J.S., Zoebisch E.G., Hearly E.F., Stewart J.J.P. J. Am. Chem. Soc. 107:1985;3902.
59. Hashimoto, M; Matsumoto, M; Terashima, S. Tetrahedron 2003, 59, 3041.