Synthetic studies directed toward the assembly of the C-glycoside fragment of the telomerase inhibitor D8646-2-6

Organic Letters

Volumn 5, Issue 16, 2003, Pages 2837-2839

  Kanai, Akira ^a   Kamino, Tomoyuki ^a   Kuramochi, Kouji ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

D 8646 2 6; GLYCOSIDE; TELOMERASE INHIBITOR;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ELECTRON; GLYCOSYLATION; ISOMERISM; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; TANDEM MASS SPECTROMETRY;

ENZYME INHIBITORS; GLYCOSIDES; TELOMERASE;

EID: 0141855265     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034873k     Document Type: Article

References (43)

1. Kimura, J.; Furui, M.; Kanda, M.; Sugiyama, M. Jpn. Kokai Tokkyo Koho 2002, 8 (in Japanese).
2. For reviews on aryl C-glycosides, see: (a) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (b) Hacksell, U.; Davis, G. D., Jr. Prog. Med. Chem. 1985, 22, 1. (c) Suzuki, K.; Matsumoto, T. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer: Berlin, 1993; Vol. 2, p 353.
3. For reviews on aryl C-glycosides, see: (a) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (b) Hacksell, U.; Davis, G. D., Jr. Prog. Med. Chem. 1985, 22, 1. (c) Suzuki, K.; Matsumoto, T. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer: Berlin, 1993; Vol. 2, p 353.
4. For reviews on aryl C-glycosides, see: (a) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (b) Hacksell, U.; Davis, G. D., Jr. Prog. Med. Chem. 1985, 22, 1. (c) Suzuki, K.; Matsumoto, T. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacs, G., Ed.; Springer: Berlin, 1993; Vol. 2, p 353.
5. For isolation and structure determination of C-glycosides, see: (a) Ayer, W. A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 7953. (b) Hochlowski, J. E.; Whittern, D. N.; Buko, A.; Alder, L.; McAlpine, J. B. J. Antibiot. 1995, 48, 614. (c) Saijo, R.; Nonaka, G.; Nishioka, I.; Chen, I.-S.; Hwang, T.-H. Chem. Pharm. Bull. 1989, 37, 2940. (d) Imamura, N.; Kakinuma, K.; Ikekawa, N.; Tanaka, H.; Omura, S. J. Antibiot. 1981, 34, 1517. (e) Traxler, P.; Fritz, H.; Fuhrer, H.; Richter, W. J. J. Antibiot. 1980, 33, 967.
6. For isolation and structure determination of C-glycosides, see: (a) Ayer, W. A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 7953. (b) Hochlowski, J. E.; Whittern, D. N.; Buko, A.; Alder, L.; McAlpine, J. B. J. Antibiot. 1995, 48, 614. (c) Saijo, R.; Nonaka, G.; Nishioka, I.; Chen, I.-S.; Hwang, T.-H. Chem. Pharm. Bull. 1989, 37, 2940. (d) Imamura, N.; Kakinuma, K.; Ikekawa, N.; Tanaka, H.; Omura, S. J. Antibiot. 1981, 34, 1517. (e) Traxler, P.; Fritz, H.; Fuhrer, H.; Richter, W. J. J. Antibiot. 1980, 33, 967.
7. For isolation and structure determination of C-glycosides, see: (a) Ayer, W. A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 7953. (b) Hochlowski, J. E.; Whittern, D. N.; Buko, A.; Alder, L.; McAlpine, J. B. J. Antibiot. 1995, 48, 614. (c) Saijo, R.; Nonaka, G.; Nishioka, I.; Chen, I.-S.; Hwang, T.-H. Chem. Pharm. Bull. 1989, 37, 2940. (d) Imamura, N.; Kakinuma, K.; Ikekawa, N.; Tanaka, H.; Omura, S. J. Antibiot. 1981, 34, 1517. (e) Traxler, P.; Fritz, H.; Fuhrer, H.; Richter, W. J. J. Antibiot. 1980, 33, 967.
8. For isolation and structure determination of C-glycosides, see: (a) Ayer, W. A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 7953. (b) Hochlowski, J. E.; Whittern, D. N.; Buko, A.; Alder, L.; McAlpine, J. B. J. Antibiot. 1995, 48, 614. (c) Saijo, R.; Nonaka, G.; Nishioka, I.; Chen, I.-S.; Hwang, T.-H. Chem. Pharm. Bull. 1989, 37, 2940. (d) Imamura, N.; Kakinuma, K.; Ikekawa, N.; Tanaka, H.; Omura, S. J. Antibiot. 1981, 34, 1517. (e) Traxler, P.; Fritz, H.; Fuhrer, H.; Richter, W. J. J. Antibiot. 1980, 33, 967.
9. For isolation and structure determination of C-glycosides, see: (a) Ayer, W. A.; Kawahara, N. Tetrahedron Lett. 1995, 36, 7953. (b) Hochlowski, J. E.; Whittern, D. N.; Buko, A.; Alder, L.; McAlpine, J. B. J. Antibiot. 1995, 48, 614. (c) Saijo, R.; Nonaka, G.; Nishioka, I.; Chen, I.-S.; Hwang, T.-H. Chem. Pharm. Bull. 1989, 37, 2940. (d) Imamura, N.; Kakinuma, K.; Ikekawa, N.; Tanaka, H.; Omura, S. J. Antibiot. 1981, 34, 1517. (e) Traxler, P.; Fritz, H.; Fuhrer, H.; Richter, W. J. J. Antibiot. 1980, 33, 967.
10. (a) Namikoshi, M.; Kobayashi, H.; Yoshimoto, T.; Meguro, S.; Akano, K. Chem. Pharm. Bull. 2000, 48, 1452.
11. (b) Evidente, A.; Conti, L.; Altomare, C.; Bottalico, A.; Sindona, G.; Segre, A. L.; Logrieco, A. Nat. Toxins 1994, 2, 4.
12. (c) Xaio, J.-Z.; Kumazawa, S.; Yoshikawa, N.; Mikawa, T.; Sato, Y. J. Antibiot. 1993, 46, 48.
13. (a) Hagiwara, H.; Kobayashi, K.; Miya, S.; Hoshi, T.; Suzuki, T.; Ando, M.; Okamoto, T.; Kobayashi, M.; Yamamoto, I.; Ohtsubo, S.; Kato, M.; Uda, H. J. Org. Chem. 2002, 67, 5969. (b) Zhang, F.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 1434.
14. (b) Zhang, F.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 1434.
15. (a) Gervay, J.; Hadd, M. J. J. Org. Chem. 1997, 62, 6961.
16. (b) Allevi, P.; Anastasia, M.; Ciuffreda, P.; Fiecchi, A.; Scala, A. J. Chem. Soc., Perkin Trans. 1 1989, 1275.
17. (c) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289.
18. (d) Hanessian, S.; Pernet, A. G. Can. J. Chem. 1974, 52, 1266.
19. (a) Kometani, T.; Kondo, H.; Fujimori, Y. Synthesis 1988, 1005.
20. (b) Rasolojaona, L.; Mastagli, P. Carbohydr. Res. 1985, 143, 246-248.
21. (c) Schmidt, R. R.; Hoffmann, M. Tetrahedron Lett. 1982, 23, 409-412.
22. (d) Eade, R. A.; Pham, H.-P. Aust. J. Chem. 1979, 32, 2483.
23. (a) Upreti, M.; Ruhela, D.; Vishwakarma, R. A. Tetrahedron 2000, 56, 6577.
24. (b) Kluge, M.; Schneider, B.; Sicker, D. Carbohydr. Res. 1997, 298, 147.
25. (a) Bonsignore, L.; Cabiddu, S.; Loy, G.; Secci, D. Heterocycles 1989, 29, 913.
26. (b) Ziegler, T.; Layh, M.; Effenberger, F. Chem. Ber. 1987, 120, 1347.
27. (c) Effenberger, F.; Ziegler, T.; Schönwäelder, K.-H.; Kesmarszky, T.; Bauer, B. Chem. Ber. 1986, 119, 3394.
28. Anomeric proton of 5 appeared at δ 5.20 with J = 7.9 Hz.
29. (a) Suzuki, K. Pure Appl. Chem. 1994, 66, 2175.
30. (b) Matsumoto, T.; Katsuki, M.; Jona, H.; Suzuki, K. J. Am. Chem. Soc. 1991, 113, 6982.
31. (c) Matsumoto, T.; Hosoya, T.; Suzuki, K. Tetrahedron Lett. 1990, 31, 4629.
32. (d) Matsumoto, T.; Katsuki, M.; Jona, H.; Suzuki, K. Tetrahedron Lett. 1989, 30, 6185.
33. (e) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1988, 29, 6935.
34. (a) Kanie, O.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1996, 37, 4551.
35. (b) Nicolaou, K. C.; Mitchell, H. J. Angew. Chem., Int. Ed. 2001, 40, 1576.
36. (a) Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379.
37. (b) Andersson, F.; Fügedi, P.; Garegg, P. J.; Nashed, M. Tetrahedron Lett. 1986, 27, 3919.
38. (c) Ito, Y.; Ogawa, T. Tetrahedron Lett. 1987, 28, 4701.
39. (a) Lokot, I. P.; Pashkovsky, F. S.; Lakhvich, F. A. Tetrahedron 1999, 55, 4783.
40. (b) Nagamitsu, T.; Sunazuka, T.; Obata, R.; Tomoda, H.; Tanaka, H.; Harigaya, Y.; Omura, S.; Smith, A. B., III. J. Org. Chem. 1995, 60, 8126.
41. (c) Cook, L.; Ternai, B.; Ghosh, P. J. Med. Chem. 1987, 30, 1017.
42. (a) Sugawara, K.; Kohno, J.; Nakanishi, N.; Hashiyama, T. Tennen Yuki. Kagoubutsu Toronkai Koen Yoshishu. 2000, 42, 661.
43. (b) Hosoya, T.; Ohashi, Y.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1996, 37, 663.