The synthesis of alisamycin, nisamycin, LL-C10037α and novel epoxyquinol and epoxyquinone analogues of manumycin A

Synthesis

Volumn , Issue 5, 1998, Pages 775-790

  Taylor, Richard J K ^a   Alcaraz, Lilian ^a,c   Kapfer Eyer, Isabelle ^a   Macdonald, Gregor ^a,b   Wei, Xudong ^a   Lewis, Norman ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

Author keywords

Alisamycin; LL C10037 ; Manumycin analogues; Nisamycin; Stille coupling

Indexed keywords

ALISAMYCIN; ANTINEOPLASTIC ANTIBIOTIC; COLABOMYCIN A; EPOXYQUINOL DERIVATIVE; EPOXYQUINONE DERIVATIVE; LL C10037ALPHA; MANUMYCIN A; NISAMYCIN; PALLADIUM; REAGENT; TRIBUTYLTIN CHLORIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STREPTOMYCES;

EID: 0031955249     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2064     Document Type: Article

References (77)

1. Buzzetti, F.; Gaümann, E.; Hütter, R.; Keller-Schierlein, W.; Neipp, L.; Prelog, V.; Zähner, H. Pharm. Acta Helv. 1963, 38, 871.
2. Schröder, K.; Zeeck, A. Tetrahedron Lett. 1973, 4995.
3. Zeeck, A.; Schröder, K.; Frobel, K.; Grote, R.; Thiericke, R. J. Antibiot. 1987, 40, 1530.
4. Zeeck, A.; Frobel, K.; Heusel, C.; Schröder, K.; Thiericke, R. J. Antibiot. 1987, 40, 1541.
5. Thiericke, R.; Stellwaag, M.; Zeeck, A.; Snatzke, G. J. Antibiot. 1987,40, 1549.
6. (a) Sattler, I.; Gröne, C.; Zeeck, A. J. Org. Chem. 1993, 58, 6583.
7. (b) Thiericke, R.; Zeeck, A.; Nakagawa, A.; Omura, S.; Herrold, R. E.; Wu, S. T. S.; Beale, J. M.; Floss, H. G. J. Am. Chem. Soc. 1990, 112, 3979.
8. Shu, Y.-Z.; Huang, S.; Wang, R. R.; Lam, K. S.; Klohr, S. E.; Volk, K. J.; Pirnik, D. M.; Wells, J. S.; Fernandes, P. B.; Patel, P. S. J. Antibiot. 1994, 47, 324.
9. (a) Kakinuma, K.; Ikekawa, N.; Nakagawa, A.; Omura, S. J. Am. Chem. Soc. 1979, 101, 3402.
10. (b) Cho, H.; Sattler, I.; Beale, J. M.; Zeeck, A.; Floss, H. G. J. Org. Chem. 1993, 58, 7925.
11. Franco, C. M. M; Maurya, R.; Vijayakumar, E. K. S; Chatterjee, S.; Blumbach, J.; Ganguli, B. N. J. Antibiot. 1991, 44, 1289.
12. Chatterjee, S.; Vijayakumar, E. K. S.; Franco, C. M. M.; Blumbach, J.; Ganguli, B. N.; Fehlhaber, H.-W.; Kogler, H. J. Antibiot. 1993, 46, 1027.
13. Hayashi, K.-I.; Nakagawa, M.; Fujita, T.; Nakayama, M. Biosci. Biotech. Biochem. 1994, 58, 1332.
14. Uosaki, Y.; Agatsuma, T.; Tanaka, T.; Saitoh, Y. J. Antibiot. 1996, 49, 1079.
15. Brodasky, T. F.; Stroman, D. W.; Dietz, A.; Mizsak, S. J. Antibiot. 1983, 36, 950.
16. Grote, R.; Zeeck, A.; Drautz, H.; Zähner, H. J. Antibiot. 1988, 41, 1178;
17. Grote, R.; Zeeck, A.; Beale, J. M. J. Antibiot. 1988, 47, 1186.
18. (a) Hayashi, K-I.; Nakagawa, M.; Fujita, T.; Tanimori, S.; Nakayama, M. J. Antibiot. 1993, 46, 1904.
19. (b) Hayashi, K-I., Nakagawa, M.; Nakayama, M. J. Antibiot. 1994, 47, 1104.
20. (c) Hayashi, K-I.; Nakagawa, M.; Fujita, T.; Tanimori, S.; Nakayama, M. J. Antibiot. 1994, 47, 1110.
21. Slechta, L.; Cialdella, J. I.; Mizsak, S. A.; Hoeksema, H. J. Antibiot. 1982, 35, 556.
22. (a) Lee, M. D.; Fantini, A. A.; Morton, G. O.; James, J. C.; Borders, D. B.; Testa, R. T. J. Antibiot. 1984, 37, 1149.
23. (b) For a correction to the original structural assignment see Shen, B.; Whittle, Y. G.; Gould, S. J.; Keszler, D. A. J. Org. Chem. 1990, 55, 4422 and references therein.
24. Box, S. J. ; Gilpin, M. L.; Gwynn, M.; Hanscomb, G.; Spear, S. R.; Brown, A. G. J. Antibiot. 1983, 36, 1631.
25. For the clarification of absolute stereochemistry see Gould, S. J.; Shen, B.; Whittle, Y. G. J. Am. Chem. Soc. 1989, 111, 7932.
26. Kohno, J.; Nishio, M.; Kawano, K.; Nakanishi, N.; Suzuki, S.-I.; Uchida, T.; Komatsubara, S. J. Antibiot. 1996, 49, 1212.
27. Hara, M.; Han, M. Proc. Natl. Acad. Sci., USA 1995, 92, 3333.
28. Hara, M.; Akasaka, K.; Akinaga, S.; Okabe, M.; Nakano, H.; Gomez, R.; Wood, D.; Uh, M.; Tamanoi, F. Proc. Natl. Acad. Sci., USA 1993, 90, 2281.
29. Omura, S.; Takeshima, H. Drugs of the Future 1994, 19, 751.
30. (a) Gould, S. J.; Kirchmeier, M. J.; LaFever, R. E. J. Am. Chem. Soc. 1996, 118, 7663 and references therein.
31. (b) Hu, Y.; Melville, C. R.; Gould, S. J.; Floss, H. G. J. Am. Chem. Soc. 1997, 119, 4301 and references therein.
32. Wipf, P.; Kim, Y. J. Org. Chem. 1994, 59, 3518;
33. Wipf, P.; Kim, Y.; Jahn, H. Synthesis 1995, 1549.
34. Corey, E. J.; Wollenberg, R. H. J. Org. Chem. 1975, 40, 3788.
35. Corey, E.J.; Wollenberg, R. H. J. Am. Chem. Soc. 1974, 96, 5581.
36. Macdonald, G.; Lewis, N.; Taylor, R. J. K. Chem. Commun. 1996, 2647.
37. Preliminary communication: Kapfer, I; Lewis, N.; Macdonald, G. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 2101.
38. McKillop, A.; McLaren, L.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. Chem. Soc., Perkin Trans. 1 1996, 1385.
39. Gautier, E. C. L.; Lewis, N.; McKillop, A.; Taylor, R. J. K. Tetrahedron Lett. 1994, 35, 8759.
40. see also: Johnson, C. R.; Miller, M. W. J. Org. Chem. 1995, 60, 6674.
41. Tamura, Y.; Yakura, T.; Haruta, J.; Kita, Y. J. Org. Chem. 1987, 52, 3927.
42. Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891.
43. McKillop, A.; McLaren, L; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1994, 2047 and references therein.
44. Rashid, A.; Read, G. J. Chem. Soc. (C) 1967, 1323.
45. Straub, T.S. Tetrahedron Lett. 1995, 36, 663.
46. McKillop, A.; Sanderson, W. R. Tetrahedron 1995, 51, 6145 and references therein.
47. Evans, E. P.; Lewis, N. J.; Kapfer, I.; Macdonald, G.; Taylor, R. J. K. Synth. Commun. 1997, 27, 1819.
48. (a) Several of the acid chlorides are commercially available; polyunsaturated acid chlorides 37b,c were prepared from the corresponding acids (oxalyl chloride, cat. DMF). The acids used to prepare 37b,c were obtained using our glutaconaldehyde methodology (Lewis, N.; McKen, P. W.; Taylor, R. J. K. Synlett 1991, 898), or from cyclohexane carboxaldehyde using Wittig methodology.
49. (b) Dr. R. Shepherd (Wyeth UK, Taplow), Personal communication.
50. Gould, S. J.; Shen, B. J. Am. Chem. Soc. 1991, 113, 684 and references therein.
51. Preliminary studies indicated that the direct deprotection of acetals 28 might be possible using Montmorillonite K10 (see ref. 31).
52. Gautier, E. C. L.; Graham, A. E.; McKillop, A.; Standen, S. P.; Taylor, R. J. K. Tetrahedron Lett. 1997, 38, 1881.
53. Weinstock, L. M.; Karady, S.; Roberts, F. E.; Hoinowski, A. M.; Brenner, G. S.; Lee, T. B. K.; Lumma, W. C.; Sletzinger, M. Tetrahedron Lett. 1975, 3979.
54. Yadav, V. K.; Kapoor, K. K. Tetrahedron 1995, 51, 8573.
55. (a) For a related organometallic addition giving a syn-hydroxy epoxide see: Carnduff, J.; Hafiz, M.; Hendrie, R.; Monaghan, F. Tetrahedron Lett. 1984, 25, 6033.
56. (b) Cronin, L.; Walton, P. H. Unpublished results.
57. Stille, J.K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
58. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
59. Negishi, E.-i.; King, A. O.; Okukado, N. J. Org. Chem. 1977, 42, 1821.
60. Davis, R. H.; Schroeder, M. E.; Mitchell, T. N. UK Patent Application GB 2112644 (31 Dec 1981).
61. see also: Amaria, A.; Mitchell, T. N. J. Organomet. Chem. 1980, 199, 49.
62. Soullez, D.; Plé, G.; Duhamel, L. J. Chem. Soc., Perkin Trans. 1 1997, 1639.
63. Alcaraz, L.; Taylor, R. J. K. Synlett 1997, 791.
64. see also Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
65. 3) was also employed in the coupling reaction (see Thibonnet, J.; Abarbi, M.; Parrain, J.-L.; Duchêne, A. Synlett 1997, 771) but this did not give a significant increase in yield.
66. Preliminary communication: Alcaraz, L.; Macdonald, G. J.; Kapfer, I.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 6619.
67. Green, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed., Wiley: N.Y., 1991.
68. Kocienski, P. Protecting Groups, Thieme: New York, 19 94.
69. For more recent procedures see Johnstone, C.; Kerr, W. J.; Scott, J. S. Chem. Commun. 1996, 341.
70. Lee, A. S. Y.; Cheng, C. L. Tetrahedron 1997, 53, 14255.
71. Jarowicki, K.; Kocienski, P. Contemp. Org. Synth. 1996, 3, 397 and references therein.
72. Lipshutz, B. H.; Harvey, D. F. Synth. Commun. 1982, 12, 267.
73. Reference 7 and Dr. H. Kogler, personal communication.
74. 1,2 may be in error (Alcaraz, L.; Ragot, J.; Taylor, R. J. K. Unpublished results). Our studies show that manumycin A probably possesses the syn-hydroxy epoxide (4S, 5R, 6S) structure [as shown for manumycin C (3)]; this finding suggests that the assignment of the anti-hydroxy epoxide configuration to other members of the manumycin family may also require stereochemical revision.
75. Rosowski, A.; Forsch, R. A.; Queener, S. F. J. Med. Chem. 1995, 38, 2615.
76. Watanabe, T.; Takeuchi, T.; Otsuka, M.; Umezawa, K. Chem. Commun. 1994, 437.
77. Buttrus, N. H.; Cornforth, Sir J.; Hitchcock, P. B.; Kumar, A.; Stuart, A. S. J. Chem. Soc., Perkin Trans. 1 1987, 851.