C-glycosyl juglone in angucycline synthesis: Total synthesis of galtamycinone, common aglycon of C-glycosyl naphthacenequinone-type angucyclines

Tetrahedron

Volumn 53, Issue 48, 1997, Pages 16533-16544

  Matsumoto, Takashi ^b   Yamaguchi, Hiroki ^a   Suzuki, Keisuke ^b  

^a KEIO UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANGUCYCLINE DERIVATIVE; ANTIBIOTIC AGENT; GALTAMYCINONE; UNCLASSIFIED DRUG;

CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030728399     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01034-X     Document Type: Conference Paper

References (47)

1. For an excellent review on the angucyclines, see: Rohr, J; Thiericke, R. Nat. Prod. Rep. 1992, 103.
2. For reviews on the synthesis of aryl C-glycoside compounds, see: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1.
3. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
4. (c) Suzuki, K.; Matsumoto, T. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G. Ed; Vol. 2, p 353; Springer: Berlin, 1993.
5. Sezaki, M.; Kondo, S.; Maeda, K.; Umezawa, H.; Ohno, M. Tetrahedron 1970, 26, 5171.
6. (a) Galtamycin: Murenets, N. V.; Smirnova, O. B. Antibiot. Khimioter. 1990, 35, 20 Murenets, N. V.; Kudinova, M. K.; Klyuev, N. A.; Chernyshev, A. I.; Shorshnev, S. V. Antibiot. Med. Biotekhnol. 1986, 31, 431. Murenets, N. V.; Kudinova, M. K.; Klyuev, N. A.; Shashkov, A. S.; Yartseva, I. V. Antibiot. Khimioter. 1988, 33, 257.
7. (a) Galtamycin: Murenets, N. V.; Smirnova, O. B. Antibiot. Khimioter. 1990, 35, 20 Murenets, N. V.; Kudinova, M. K.; Klyuev, N. A.; Chernyshev, A. I.; Shorshnev, S. V. Antibiot. Med. Biotekhnol. 1986, 31, 431. Murenets, N. V.; Kudinova, M. K.; Klyuev, N. A.; Shashkov, A. S.; Yartseva, I. V. Antibiot. Khimioter. 1988, 33, 257.
8. (a) Galtamycin: Murenets, N. V.; Smirnova, O. B. Antibiot. Khimioter. 1990, 35, 20 Murenets, N. V.; Kudinova, M. K.; Klyuev, N. A.; Chernyshev, A. I.; Shorshnev, S. V. Antibiot. Med. Biotekhnol. 1986, 31, 431. Murenets, N. V.; Kudinova, M. K.; Klyuev, N. A.; Shashkov, A. S.; Yartseva, I. V. Antibiot. Khimioter. 1988, 33, 257.
9. 1: Yamada, T.; Suzuki, K.; Nohara, C.; Kozasa, T. JP Patent 0272 884, 1990; Chem. Abstr. 1991, 113, 229690z.
10. 1: Yamada, T.; Suzuki, K.; Nohara, C.; Kozasa, T. JP Patent 0272 884, 1990; Chem. Abstr. 1991, 113, 229690z.
11. (c) C57: Arnone, A.; Cardillo, R.; Nasini, G.; Vajna de Pava, O.; Quaroni, S. Phytochemistry 1988, 27, 3611.
12. Y. Naruta and K. Maruyama In The Chemistry of Functional Groups: The Chemistry of the Quinonoid Compounds; Patai, S.; Rappoport, Z. Eds; Vol. 2, Chap. 8, p 241; Wiley: New York, 1988.
13. Diels-Alder reaction of naphthoquinone derivatives is a standard approach to benz[a]anthraquinone derivatives. For recent examples in relation to the angucycline synthesis, see: (a) Boyd, V. A.; Sulikowski, G. A. J. Am. Chem. Soc. 1995, 117, 8472.
14. (b) Krohn, K.; Khanbabaee, K.; Jones, P. G. Liebigs Ann. Chem. 1995, 1981.
15. For preliminary reports of this work, see: (a) Matsumoto, T; Sohma, T.; Yamaguchi, H.; Suzuki, K. Chem. Lett. 1995, 677.
16. (b) Matsumoto, T; Sohma, T.; Yamaguchi, H.; Suzuki, K. Synlett. 1996, 433.
17. C-Olivosylation of 1-acetoxy-4-methoxy-5-naphthol was performed in good yield by the O→C-glycoside rearrangement. Hosoya, T.; Ohashi, Y.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1996, 37, 663.
18. For the 0→ C-glycoside rearrangement, see: (a) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1988, 29, 6935.
19. (b) Matsumoto, T; Katsuki, M.; Jona, H.; Suzuki, K. Ibid. 1989, 30, 6185.
20. (c) Matsumoto, T; Hosoya, T.; Suzuki, K. Ibid. 1990, 31, 4629.
21. (d) Matsumoto, T; Katsuki, M.; Jona, H.; Suzuki, K. J. Am. Chem. Soc. 1991, 113, 6982.
22. (e) Matsumoto, T; Hosoya, T.; Suzuki, K. Synlett 1991, 709.
23. Also see, (f) Matsumoto, T; Hosoya, T.; Suzuki, K. J. Am. Chem. Soc. 1992, 114, 3568.
24. (g) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. Ibid. 1994, 116, 1004.
25. (i) Kometani, T.; Kondo, H.; Fujimori, Y. Synthesis 1988, 1005.
26. For the synthetic studies along the same lines, see: Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 225. Andrew, F. L.; Larsen, D. S. Tetrahedron Lett. 1994, 35, 8693.
27. For the synthetic studies along the same lines, see: Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 225. Andrew, F. L.; Larsen, D. S. Tetrahedron Lett. 1994, 35, 8693.
28. Another effective approach to the angucyclines involves the C-glycoside formation to the fully assembled tetracyclic skeleton. For example, see the first total synthesis of antibiotic C104, a prototypical banz[a]anthracene-type compound: Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Synlett 1995, 263. Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Tetrahedron 1995, 51, 7347.
29. Another effective approach to the angucyclines involves the C-glycoside formation to the fully assembled tetracyclic skeleton. For example, see the first total synthesis of antibiotic C104, a prototypical banz[a]anthracene-type compound: Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Synlett 1995, 263. Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Tetrahedron 1995, 51, 7347.
30. For other efficient approach to a C-glycosyl juglone, see: ref. 6a.
31. For the benzyne-furan cycloaddition reaction, see: (a) Matsumoto, T.; Hosoya, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1991, 32, 6735.
32. See also: (d) Giles, R. G. F.; Sargent, M. V.; Sianipar, H. J. Chem. Soc., Perkin Trans. 1 1991, 1571.
33. (e) Giles, R. G. F.; Hughes, A. B.; Sargent, M. V. Ibid. 1991, 1581. Also see, ref. 9f, g.
34. R. C. Larock, B. Riefling, and C. A. Fellows, J. Org. Chem., 43, 131 (1978).
35. G. Jas, Synthesis, 1991, 965.
36. (a) Bolitt, V.; Mioskowski, C.; Lee, S.-G.; Falck, J. R. J. Org. Chem. 1990, 55, 5812.
37. (b) Beau, J.-M.; Jaurand, G.; Esnault, J.; Sinay, P. Tetrahedron Lett. 1987, 28, 1105.
38. (c) Fraser-Reid, B.; Kelly, D. R.; Tulshian, D. B.; Ravi, P. S. J. Carbohydr. Chem. 1983, 2, 105.
39. Tamura, Y.; Fukata, F.; Sasho, M.; Tsugoshi, T.; Kita, Y. J. Org. Chem. 1985, 50, 2273. Tamura, Y.; Sasho, M.; Nakagawa, K. Tsugoshi, T.; Kita, Y. J. Org. Chem. 1984, 49, 473. Tamura, Y.; Akai, S.; Sasho, M.; Kita, Y. Tetrahedron Lett. 1984, 25, 1167. Tamura, Y.; Sasho, M.; Akai, S.; Wada, A.; Kita, Y. Tetrahedron 1984, 40, 4539.
40. Tamura, Y.; Fukata, F.; Sasho, M.; Tsugoshi, T.; Kita, Y. J. Org. Chem. 1985, 50, 2273. Tamura, Y.; Sasho, M.; Nakagawa, K. Tsugoshi, T.; Kita, Y. J. Org. Chem. 1984, 49, 473. Tamura, Y.; Akai, S.; Sasho, M.; Kita, Y. Tetrahedron Lett. 1984, 25, 1167. Tamura, Y.; Sasho, M.; Akai, S.; Wada, A.; Kita, Y. Tetrahedron 1984, 40, 4539.
41. Tamura, Y.; Fukata, F.; Sasho, M.; Tsugoshi, T.; Kita, Y. J. Org. Chem. 1985, 50, 2273. Tamura, Y.; Sasho, M.; Nakagawa, K. Tsugoshi, T.; Kita, Y. J. Org. Chem. 1984, 49, 473. Tamura, Y.; Akai, S.; Sasho, M.; Kita, Y. Tetrahedron Lett. 1984, 25, 1167. Tamura, Y.; Sasho, M.; Akai, S.; Wada, A.; Kita, Y. Tetrahedron 1984, 40, 4539.
42. Tamura, Y.; Fukata, F.; Sasho, M.; Tsugoshi, T.; Kita, Y. J. Org. Chem. 1985, 50, 2273. Tamura, Y.; Sasho, M.; Nakagawa, K. Tsugoshi, T.; Kita, Y. J. Org. Chem. 1984, 49, 473. Tamura, Y.; Akai, S.; Sasho, M.; Kita, Y. Tetrahedron Lett. 1984, 25, 1167. Tamura, Y.; Sasho, M.; Akai, S.; Wada, A.; Kita, Y. Tetrahedron 1984, 40, 4539.
43. Turner, F. A.; Gearien, J. E. J. Org. Chem. 1959, 24, 1952.
44. Recent review: Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
45. Kouklovsky, C.; Pouilhés, A.; Langlois, Y. J. Am. Chem. Soc. 1990, 112, 6672.
46. 3 generously provided by Dr. Shinichi Kondo, Institute of Microbial Chemistry.
47. Brinkley, S. R., Jr. J. Am. Chem. Soc. 1940, 62, 3524.