Synthetic studies on tautomycin synthesis of segment B

Tetrahedron

Volumn 53, Issue 14, 1997, Pages 5083-5102

  Tsuboi, Katsunori ^a   Ichikawa, Yoshiyasu ^a   Naganawa, Atsushi ^a   Isobe, Minoru ^a   Ubukata, Makoto ^b   Isono, Kiyoshi ^c  

^a NAGOYA UNIVERSITY   (Japan)

^b TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^c TOKAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TAUTOMYCIN;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0030900925     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00228-7     Document Type: Article

References (55)

1. Cheng, X.-C.; Kihara, T.; Kusakabe, H.; Magae, J.; Kobayashi, Y.; Fang, R.-P.; Ni, Z.-F.; Shen, Y.-C.; Ko, K.; Yamaguchi, I.; Isono, K. J. Antibiot. 1987, 40, 907.
2. Magae, J.; Watanabe, C.; Osada, H.; Cheng, X.-C.; Isono, K. J. Antibiot. 1988, 41, 932.
3. (a) Magae, J.; Osada, H.; Fujiki, H.; Saido, T. C.; Suzuki, K.; Nagai, K.; Yamasaki, M.; Isono, K. Proc. Japan Acad. Ser. B 1990, 66, 209.
4. (b) MacKintosh, C.; Klumpp, S. FEBS Lett. 1990, 277, 137.
5. (c) Hori, M.; Magae, J.; Han, Y.-G.; Hartshorne, D. J.; Karaki, H. FEBS Lett. 1991, 285, 145.
6. (d) Magae, J.; Hino, A.; Isono, K.; Nagai, K. J. Antibiot. 1992, 45, 246.
7. (e) Kurisaki, T.; Magae, J.; Isono, K.; Nagai, K.; Yamasaki, M. J. Antibiot. 1992, 45, 252.
8. Tachibana, K.; Scheuer, P. J.; Tsukitani, Y.; Kikuchi, H.; Engen, D. V.; Clardy, J.; Gopichand, Y.; Schmitz, F. J. J. Am. Chem. Soc. 1981, 103, 2469.
9. Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K. Fujita, S.; Furuya, T. J. Am. Chem. Soc. 1986, 108, 2780.
10. Carmichael,W. W.; Beasley, V.; Bunner, D. L.; Eloff, J. N.; Falconer, I.; Gorham, P.; Harada, K.; Krishnamurthy, T.; Yu, M.-J.; Moore, R. E.; Rinehart, K.; Runnegar, M.; Skulberg, O. M.; Watanabe, M. Toxicon 1988, 26, 971.
11. Rinehart, K. L.; Harada, K.; Namikoshi, M.; Chen, C.; Harvis, C. A.; Munro, M. H. G.; Blunt, J. W.; Mulligan, P. E.; Beasley, V. R.; Dahlem, A. M.; Carmichael, W. W. J. Am. Chem. Soc. 1988, 110, 8557.
12. (a) Ubukata, M.; Cheng, X.-C.; Isono, K. J. Chem. Soc., Chem. Commun. 1990, 244.
13. (b) Cheng, X.-C.; Ubukata, M.; Isono, K. J. Antibiot. 1990, 43, 809.
14. (c) Ubukata, M.; Cheng, X.-C.; Isobe, M.; Isono, K. J. Chem. Soc., Perkin Trans, 1, 1993, 617.
15. (a) Nakamura, S.; Shibasaki, M. Tetrahedron Lett. 1994, 35, 4145.
16. (b) Shimizu, S.; Nakamura, S.; Nakada, M.; Shibasaki, M. Tetrahedron 1996, 52, 13363.
17. (c) Maurer, K. W.; Armstrong, R. W. J. Org. Chem. 1996, 61, 3106.
18. (a) Oikawa, M.; Oikawa, H.; Ichihara, A. Tetrahedron Lett. 1993, 34, 4797.
19. (b) Oikawa, H.; Oikawa, M.; Ueno, T.; Ichihara, A. Tetrahedron Lett. 1994, 35, 4809.
20. (c) Oikawa, M.; Ueno, T.; Oikawa, H.; Ichihara, A. J. Org. Chem. 1995, 60, 5048.
21. (d) Ueno, T.; Oikawa, M.; Oikawa, H.; Ichihara, A. Biosci. Biotech. Biochem. 1995, 59, 2104.
22. Isobe, M.; Ichikawa, Y.; Bai, D.-L.; Masaki, H.; Goto, T. Tetrahedron 1987, 43, 4767.
23. (a) Takai, A.; Murata, M.; Torigoe, K.; Isobe, M.; Mieskes, G.; Yasumoto, T. Biochem. J. 1992, 284, 539.
24. (b) Takai, A.; Sasaki, K.; Nagai, H.; Mieskes, G.; Isobe, M.; Isono, K.; Yasumoto, T. Biochem. J. 1995, 306, 657.
25. Sugiyama, Y.; Ohtani, I. I.; Isobe, M.; Takai, A.; Ubukata, M.; Isono, K. Bioorg. Med. Chem. Lett. 1996, 6, 3.
26. (a) Ichikawa, Y.; Naganawa, A.; Isobe, M. Synlett 1993, 737.
27. (b) Ichikawa, Y.; Tsuboi, K.; Naganawa, A.; Isobe, M. Synlett 1993, 907.
28. (c) Naganawa, A.; Ichikawa, Y.; Isobe, M. Tetrahedron 1994, 50, 8969.
29. (d) Jiang, Y.; Ichikawa, Y.; Isobe, M. Synlett 1995, 285.
30. (e) Jiang , Y.; Isobe, M. Tetrahedron 1996, 52, 2877.
31. Ichikawa, Y.; Tsuboi, K.; Jiang, Y.; Naganawa, A.; Isobe, M. Tetrahedron Lett. 1995, 36, 7101.
32. Oikawa et al. reported tris-TBS-tautomycin 4 resisted deprotection by using aqueous hydrogen fluoride or poly(hydrogen fluoride) pyridine complex. See the references; (a) Oikawa, M.; Ueno, T.; Oikawa, H.; Ichihara, A. J. Synth. Org. Chem. Jpn. 1995, 53, 1123.
33. (b) Oikawa, H.; Oikawa, M.; Ichihara, A.; Ubukata, M.; Isono, K. Biosci. Biotech. Biochem. 1994, 58, 1933.
34. Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
35. Ichikawa, Y.; Isobe, M.; Ubukata, M.; Isono, K. Biosci. Biotech. Biochem. 1993, 57, 1382.
36. (a) Midland, M. M.; McDowell, D. C.; Hatch, R. L.; Tramontano, A. J. Am. Chem. Soc. 1980, 102, 867.
37. (b) Midland, M. M.; Graham, R. S. Org. Synth., Coll. Vol. VII. 1990, 402.
38. 3 signals appearing at δ 3.55 and 3.59.
39. (a) Brewster, P.; Hiron, F.; Hughes, E. D.; Ingold, C. K.; Rao, P. A. D. S. Nature 1950, 166, 179.
40. (b) Mori, K. Tetrahedron 1976, 32, 1101.
41. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139.
42. (a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943.
43. (b) Christ, W. J.; Cha, J. K.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3947.
44. (c) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247.
45. (d) Evans, D. A.; Kaldor, S. W. J. Org. Chem. 1990, 55, 1698.
46. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
47. (b) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. The relative stereochemistry at C-23 and C-24 of tautomycin has been confirmed by the synthesis of p-methoxybenzylidene acetal of the 1,3-diol at C-23 and C-24, and its structural analysis by MacroModel. See the reference 8(c) and 18.
48. Johansson, R.; Samuelsson, B. J. Chem. Soc., Chem. Commun. 1984, 201.
49. 25 -27.0° should be +27.0°.
50. (a) Ma, P.; Martin, V. S.; Masamune, S.; Sharpless, K. B.; Viti, S. M. J. Org. Chem. 1982, 47, 1378.
51. (b) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
52. 2 symmetry nature of 35 provided a mixture of 36 and 37, which are essentially identical stereoisomer by removal of the benzyl group.
53. Roush, W. R.; Adam, M. A.; Peseckis, S. M. Tetrahedron Lett. 1983, 24, 1377.
54. Hanessian, S. Aldrichimica Acta 1989, 22, 3.
55. Williams, D. R.; Sit, S.-Y. J. Am. Chem. Soc. 1984, 106, 2949.