Synthesis of acyclic and heterocyclic natural products utilizing cyclitols as novel chiral building blocks

Chemical Communications

Volumn , Issue 9, 1997, Pages 807-813

  Chida, Noritaka ^a   Ogawa, Seiichiro ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; CYCLITOL; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE;

EID: 0031008911     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a603301f     Document Type: Article

References (62)

1. A. Fischli, in Modern Synthetic Methods, ed. R. Scheffold, Verlag Sauerländer, Frankfurt, 1980, p. 269; K. Drauz, A. Kleeman and J. Martens, Angew. Chem., Int. Ed. Engl., 1982, 21, 584.
2. A. Fischli, in Modern Synthetic Methods, ed. R. Scheffold, Verlag Sauerländer, Frankfurt, 1980, p. 269; K. Drauz, A. Kleeman and J. Martens, Angew. Chem., Int. Ed. Engl., 1982, 21, 584.
3. K. Mori, in The Total Synthesis of Natural Products, ed. J. ApSimon, Wiley, New York, 1981, p. 1; T.-L. Ho, Enantioselective Synthesis, Wiley, New York, 1992.
4. K. Mori, in The Total Synthesis of Natural Products, ed. J. ApSimon, Wiley, New York, 1981, p. 1; T.-L. Ho, Enantioselective Synthesis, Wiley, New York, 1992.
5. J. W. Scott, in Asymmetric Synthesis, ed. J. D. Morrison and J. W. Scott, Academic Press, Florida, 1984, vol. 4, p. 1.
6. S. Hanessian, Total Synthesis of Natural Products: The 'Chiron' Approach, Pergamon Press, Oxford, 1983; B. Fraser-Reid and R. Tsang, in Strategies and Tactics in Organic Synthesis, ed. T. Lindberg and D. Barton, Academic Press, San Diego, 1989, vol. 2, p. 123.
7. S. Hanessian, Total Synthesis of Natural Products: The 'Chiron' Approach, Pergamon Press, Oxford, 1983; B. Fraser-Reid and R. Tsang, in Strategies and Tactics in Organic Synthesis, ed. T. Lindberg and D. Barton, Academic Press, San Diego, 1989, vol. 2, p. 123.
8. L. Anderson, in The Carbohydrates; Chemistry and Biochemistry, ed. W. Pigman and D. Horton, Academic Press, New York, 1972, vol. 1a, p. 519.
9. (a) J. van Alphen, Ind. Eng. Chem., 1951, 43, 141;
10. (b) N. Chida, M. Suzuki, M. Suwama and S. Ogawa, J. Carbohydr. Chem., 1989, 8, 319.
11. H. Fukami, H.-S. Koh, T. Sakata and M. Nakajima, Tetrahedron Lett., 1967, 4771; 1968, 1701.
12. H. Fukami, H.-S. Koh, T. Sakata and M. Nakajima, Tetrahedron Lett., 1967, 4771; 1968, 1701.
13. N. Chida, T. Tobe and S. Ogawa, Tetrahedron Lett., 1994, 35, 7249.
14. A. S. Cieplak, J. Am. Chem. Soc., 1981, 103, 4540; A. S. Cieplak, B. D. Tait and C. R. Johnson, J. Am. Chem. Soc., 1989, 111, 8447.
15. A. S. Cieplak, J. Am. Chem. Soc., 1981, 103, 4540; A. S. Cieplak, B. D. Tait and C. R. Johnson, J. Am. Chem. Soc., 1989, 111, 8447.
16. Y. Watanabe, A. Oka, Y. Shimizu and S. Ozaki, Tetrahedron Lett., 1990, 31, 2613; S. Ozaki, L. Ling, T. Ogasawara, Y. Watanabe and M. Hirata, Carbohydr. Res., 1994, 259, 307; G. M. Salamonczyk and M. Pietrusiewicz, Tetrahedron Lett., 1994, 35, 4233.
17. Y. Watanabe, A. Oka, Y. Shimizu and S. Ozaki, Tetrahedron Lett., 1990, 31, 2613; S. Ozaki, L. Ling, T. Ogasawara, Y. Watanabe and M. Hirata, Carbohydr. Res., 1994, 259, 307; G. M. Salamonczyk and M. Pietrusiewicz, Tetrahedron Lett., 1994, 35, 4233.
18. Y. Watanabe, A. Oka, Y. Shimizu and S. Ozaki, Tetrahedron Lett., 1990, 31, 2613; S. Ozaki, L. Ling, T. Ogasawara, Y. Watanabe and M. Hirata, Carbohydr. Res., 1994, 259, 307; G. M. Salamonczyk and M. Pietrusiewicz, Tetrahedron Lett., 1994, 35, 4233.
19. (a) V. I. Shvets, B. A. Klyashchitskii, A. E. Stepanov and R. P. Evstigneeva, Tetrahedron, 1973, 29, 331;
20. (b) P. J. Garegg, B. Lindberg, I. Kvarnstrom and S. C. T. Svensson, Carbohydr. Res., 1985, 139, 209; S. Ozaki, Y. Watanabe, T. Ogasawara, Y. Kondo, N. Shiotani, H. Nishii and T. Matsuki, Tetrahedron Lett., 1986, 27, 3157.
21. (b) P. J. Garegg, B. Lindberg, I. Kvarnstrom and S. C. T. Svensson, Carbohydr. Res., 1985, 139, 209; S. Ozaki, Y. Watanabe, T. Ogasawara, Y. Kondo, N. Shiotani, H. Nishii and T. Matsuki, Tetrahedron Lett., 1986, 27, 3157.
22. S. J. Angyal, M. E. Tate and S. D. Gero, J. Chem. Soc., 1961, 4116; C. Jiang and D. C. Baker, J. Carbohydr. Chem., 1986, 5, 615.
23. S. J. Angyal, M. E. Tate and S. D. Gero, J. Chem. Soc., 1961, 4116; C. Jiang and D. C. Baker, J. Carbohydr. Chem., 1986, 5, 615.
24. N. Chida, E. Yamada and S. Ogawa, J. Carbohydr. Chem., 1988, 7, 555.
25. (a) N. Chida, Y. Furuno and S. Ogawa, J. Chem. Soc., Chem. Commun., 1989, 1230;
26. (b) N. Chida, Y. Furuno, H. Ikemoto and S. Ogawa, Carbohydr. Res., 1992, 237, 185.
27. N. Chida, H. Ikemoto, A. Noguchi, S. Amano and S. Ogawa, Nat. Prod. Lett., 1995, 6, 295.
28. N. Chida, K. Koizumi, Y. Kitada, C. Yokoyama and S. Ogawa, J. Chem. Soc., Chem. Commun., 1994, 111.
29. S. J. Angyal and R. M. Hoskinson, Methods Carbohydr. Chem., 1963, 2, 87.
30. N. Chida, T. Tobe and S. Ogawa, Tetrahedron Lett., 1991, 32, 1063.
31. (a) N. Chida, T. Tobe, S. Okada and S. Ogawa, J. Chem. Soc., Chem. Commun., 1992, 1064;
32. (b) N. Chida, T. Tobe, K. Murai, K. Yamazaki and S. Ogawa, Heterocycles, 1994, 38, 2383.
33. H. Paulsen and F. R. Heiker, Liebigs Ann. Chem., 1981, 2180.
34. N. Chida, K. Yamada and S. Ogawa, Chem. Lett., 1992, 687; J. Chem. Soc., Perkin Trans. 1, 1993, 1957.
35. N. Chida, K. Yamada and S. Ogawa, Chem. Lett., 1992, 687; J. Chem. Soc., Perkin Trans. 1, 1993, 1957.
36. N. Chida, K. Yamada, M. Suzuki and S. Ogawa, J. Carbohydr. Chem., 1992, 11, 137.
37. (a) N. Chida, T. Tobe, M. Suwama, M. Ohtsuka and S. Ogawa, J. Chem. Soc., Chem. Commun., 1990, 994;
38. (b) J. Chem. Soc. Perkin Trans. 1, 1992, 2667.
39. N. Chida, T. Tanikawa, T. Tobe and S. Ogawa, J. Chem. Soc., Chem. Commun., 1994, 1247.
40. N. Chida, T. Tobe, M. Yoshinaga, K. Osaka and S. Ogawa, Carbohydr. Lett., 1996, 2, 47.
41. N. Chida, K. Nakazawa, S. Ninomiya, S. Amano, K. Koizumi, J. Inaba and S. Ogawa, Carbohydr. Lett., 1995, 1, 335.
42. S. Ogawa and A. Isaka, Carbohydr. Res., 1991, 210, 105; S. Ogawa, A. Ohdate, K. Ohnishi, T. Tanikawa, H. Kimura and N. Chida, Carbohydr. Lett., 1995, 1, 255.
43. S. Ogawa and A. Isaka, Carbohydr. Res., 1991, 210, 105; S. Ogawa, A. Ohdate, K. Ohnishi, T. Tanikawa, H. Kimura and N. Chida, Carbohydr. Lett., 1995, 1, 255.
44. H. Paulsen, W. van Deyn and W. Röben, Liebigs Ann. Chem., 1984, 433.
45. S. Bath, D. C. Billington, S. D. Gero, B. Quiclet-Sire and M. Samadi, J. Chem. Soc., Chem. Commun., 1994, 1495.
46. T. Akiyama, H. Shima and S. Ozaki, Synlett, 1991, 831; T. Akiyama, H. Shima, M. Ohnari, T. Okazaki and S. Ozaki, Bull. Chem. Soc. Jpn., 1993, 66, 3760.
47. T. Akiyama, H. Shima and S. Ozaki, Synlett, 1991, 831; T. Akiyama, H. Shima, M. Ohnari, T. Okazaki and S. Ozaki, Bull. Chem. Soc. Jpn., 1993, 66, 3760.
48. A. P. Kozikowski, J. J. Kiddle, T. Frew, M. Berggren and G. Powis, J. Med. Chem., 1995, 38, 1053; A. P. Kozikowski, V. I. Ognyanov, A. H. Fauq, S. R. Nahhorski and R. A. Wilcox, J. Am. Chem. Soc., 1993, 115, 4429 and references cited therein.
49. A. P. Kozikowski, J. J. Kiddle, T. Frew, M. Berggren and G. Powis, J. Med. Chem., 1995, 38, 1053; A. P. Kozikowski, V. I. Ognyanov, A. H. Fauq, S. R. Nahhorski and R. A. Wilcox, J. Am. Chem. Soc., 1993, 115, 4429 and references cited therein.
50. T. Akiyama, N. Takechi and S. Ozaki, Tetrahedron Lett., 1990, 31, 1433; T. Akiyama, N. Takechi, S. Ozaki and K. Shiota, Bull. Chem. Soc. Jpn., 1992, 65, 366.
51. T. Akiyama, N. Takechi and S. Ozaki, Tetrahedron Lett., 1990, 31, 1433; T. Akiyama, N. Takechi, S. Ozaki and K. Shiota, Bull. Chem. Soc. Jpn., 1992, 65, 366.
52. C. Liu, S. R. Nahorski and B. V. L. Potter, J. Chem. Soc., Chem. Commun., 1991, 1014; Carbohydr. Res., 1992, 234, 107; D. Lampe, C. Liu and B. V. L. Potter, J. Med. Chem., 1994, 37, 907; C. Liu, J. Al-Hafidh, J. Westwick and B. V. L. Potter, Bioorg. Med. Chem., 1994, 2, 253.
53. C. Liu, S. R. Nahorski and B. V. L. Potter, J. Chem. Soc., Chem. Commun., 1991, 1014; Carbohydr. Res., 1992, 234, 107; D. Lampe, C. Liu and B. V. L. Potter, J. Med. Chem., 1994, 37, 907; C. Liu, J. Al-Hafidh, J. Westwick and B. V. L. Potter, Bioorg. Med. Chem., 1994, 2, 253.
54. C. Liu, S. R. Nahorski and B. V. L. Potter, J. Chem. Soc., Chem. Commun., 1991, 1014; Carbohydr. Res., 1992, 234, 107; D. Lampe, C. Liu and B. V. L. Potter, J. Med. Chem., 1994, 37, 907; C. Liu, J. Al-Hafidh, J. Westwick and B. V. L. Potter, Bioorg. Med. Chem., 1994, 2, 253.
55. C. Liu, S. R. Nahorski and B. V. L. Potter, J. Chem. Soc., Chem. Commun., 1991, 1014; Carbohydr. Res., 1992, 234, 107; D. Lampe, C. Liu and B. V. L. Potter, J. Med. Chem., 1994, 37, 907; C. Liu, J. Al-Hafidh, J. Westwick and B. V. L. Potter, Bioorg. Med. Chem., 1994, 2, 253.
56. N. Chida, K. Yamada and S. Ogawa, J. Chem. Soc., Chem. Commun., 1991, 588; J. Chem. Soc., Perkin Trans. 1, 1992, 1131.
57. N. Chida, K. Yamada and S. Ogawa, J. Chem. Soc., Chem. Commun., 1991, 588; J. Chem. Soc., Perkin Trans. 1, 1992, 1131.
58. T. Akiyama, H. Nishimoto, T. Kuwata and S. Ozaki, Bull. Chem. Soc. Jpn., 1994, 67, 180; T. Akiyama, K. Ishikawa and S. Ozaki, Chem. Lett., 1994, 627; T. Aakiyama, K. Okada and S. Ozaki, Tetrahedron Lett., 1992, 33, 5763; T. Akiyama, H. Horiguchi, T. Ida and S. Ozaki, Chem. Lett., 1995, 975 and references cited therein.
59. T. Akiyama, H. Nishimoto, T. Kuwata and S. Ozaki, Bull. Chem. Soc. Jpn., 1994, 67, 180; T. Akiyama, K. Ishikawa and S. Ozaki, Chem. Lett., 1994, 627; T. Aakiyama, K. Okada and S. Ozaki, Tetrahedron Lett., 1992, 33, 5763; T. Akiyama, H. Horiguchi, T. Ida and S. Ozaki, Chem. Lett., 1995, 975 and references cited therein.
60. T. Akiyama, H. Nishimoto, T. Kuwata and S. Ozaki, Bull. Chem. Soc. Jpn., 1994, 67, 180; T. Akiyama, K. Ishikawa and S. Ozaki, Chem. Lett., 1994, 627; T. Aakiyama, K. Okada and S. Ozaki, Tetrahedron Lett., 1992, 33, 5763; T. Akiyama, H. Horiguchi, T. Ida and S. Ozaki, Chem. Lett., 1995, 975 and references cited therein.
61. T. Akiyama, H. Nishimoto, T. Kuwata and S. Ozaki, Bull. Chem. Soc. Jpn., 1994, 67, 180; T. Akiyama, K. Ishikawa and S. Ozaki, Chem. Lett., 1994, 627; T. Aakiyama, K. Okada and S. Ozaki, Tetrahedron Lett., 1992, 33, 5763; T. Akiyama, H. Horiguchi, T. Ida and S. Ozaki, Chem. Lett., 1995, 975 and references cited therein.
62. J. J. Kiddle, Chem. Rev., 1995, 95, 2189.