Total Synthesis of Galtamycinone, the Common Aglycon of the C-Glycosyl Naphthacenequinone Antibiotics

Synlett

Volumn 1996, Issue 5, 1996, Pages 433-434

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

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000190254     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5461     Document Type: Article

References (25)

1. (a) 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.
2. (a) 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.
3. (a) 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.
4. (b) Arnone, A.; Cardillo, R.; Nasini, G.; Vajna de Pava, O.; Quaroni, S. Phytochemistry 1988, 27, 3611.
5. (c) Yamada, T.; Suzuki, K.; Nohara, C.; Kozasa, T. JP Patent 0272 884, 1990; Chem. Abstr. 1991, 113, 229690z.
6. Reviews on the synthesis of aryl C-glycoside compounds: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (c) Suzuki, K.; Matsumoto, T. in "Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products," ed by Lukacs, G.: Springer, Berlin (1993), Vol. 2, p 353.
7. Reviews on the synthesis of aryl C-glycoside compounds: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (c) Suzuki, K.; Matsumoto, T. in "Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products," ed by Lukacs, G.: Springer, Berlin (1993), Vol. 2, p 353.
8. Reviews on the synthesis of aryl C-glycoside compounds: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (c) Suzuki, K.; Matsumoto, T. in "Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products," ed by Lukacs, G.: Springer, Berlin (1993), Vol. 2, p 353.
9. Recent articles on the total synthesis of aryl C-glycoside antibiotics: (a) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. (b) Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Synlett 1995, 263. (c) Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Tetrahedron 1995, 51, 7347.
10. Recent articles on the total synthesis of aryl C-glycoside antibiotics: (a) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. (b) Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Synlett 1995, 263. (c) Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Tetrahedron 1995, 51, 7347.
11. Recent articles on the total synthesis of aryl C-glycoside antibiotics: (a) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004. (b) Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Synlett 1995, 263. (c) Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Kurata, S.; Suzuki, K. Tetrahedron 1995, 51, 7347.
12. Matsumoto, T.; Sohma, T.; Yamaguchi, H.; Suzuki, K. Chem. Lett. 1995, 677.
13. Matsumoto, T.; Hosoya, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1991, 32, 6735. Also see, ref. 3.
14. 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.
15. 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.
16. 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.
17. 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.
18. Turner, F. A.; Gearien, J. E. J. Org. Chem. 1959, 24, 1952.
19. Recent review: Gant, T. G.; Meyers, A. I. Tetrahedron 1994, 50, 2297.
20. 3OH: C, 64.72; H, 5.43. Found: C, 64.66; H, 5.12.
21. Kouklovsky, C.; Pouilhés, A.; Langlois, Y. J. Am. Chem. Soc. 1990, 112, 6672. The attempted hydrolysis under acidic conditions, conventionally employed, caused the removal of the benzyl protective group.
22. Judging from the TLC monitoring, the cycloaddition proceeds in a temperature range of ca. -30 to 0°C. It was found, however, that careful admixing of 2 and the anion of 6 at lower temperature is required to avoid concomitant formation of the isomeric adduct due to an increase in the internal temperature.
23. Naruta, Y.; Maruyama, K. in "The Chemistry of Functional Group: The Chemistry of the Quinonoid Compounds," ed by Patai, S. and Rappoport, Z., Wiley, New York (1988), Vol. 2, Chap. 8, p 241.
24. 14 kindly provided by Dr. Kondo, Institute of Microbial Chemistry.
25. Sezaki, M.; Kondo, S.; Maeda, K.; Umezawa, H.; Ohno, M. Tetrahedron 1970, 26, 5171.