Concise approach to 1-thiaHydantocidin

Synthetic Communications

Volumn 26, Issue 1, 1996, Pages 75-81

  Lamberth, Clemens ^a   Blarer, Stefan ^a  

^a Sandoz Agro Ltd   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

1 THIAHYDANTOCIDIN; HERBICIDE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030066138     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003864     Document Type: Article

References (44)

1. a) H. Haruyama, T. Takayama, T. Kinoshita, M. Kondo, M. Nakajima, T. Haneishi, J. Chem. Soc. Perkin Trans. I 1991, 1637;
2. b) M. Nakajima, K. Itoi, Y. Takamatsu, T. Kinoshita, T. Okazaki, K. Kawakubo, M. Shindo, T. Honma, M. Tohjigamori, T. Haneishi, J. Antibiot. 1991, 44, 293;
3. c) Sankyo, Eur. Pat. Appl. 0 232 572 A, 19.08.1989;
4. d) Sankyo, US. Pat. 4,952,234, 29.07.1988.
5. Ciba-Geigy, DE Pat. 41 29 616 A, 10.09.1990.
6. Mitsubishi Kasei, Jap. Pat. 04222589 A, 19.12.1990.
7. For synthetic spironucleosides see: a) A. Kittaka, H. Tanaka, Y. Odanaka, K. Ohnuki, K. Yamaguchi, T. Miyasaka, J. Org. Chem, 1994, 59, 3636; b) M. Yokoyama, K. Sujino, M. Irie, N. Yamazaki, T. Hiyama, N. Yamada, H. Togo, J. Chem. Soc. Perkin Trans. I 1991, 2801; c) M. Yokoyama, N. Yamada, H. Togo, Chem. Lett. 1990, 753; d) M. Yokoyama, N. Yamada, Tetrahedron Lett. 1989, 30, 3675; e) J.P. Ferris, B. Devadas, J. Org. Chem. 1987, 52, 2355; f) J.P. Ferris, B. Devadas, Tetrahedron Lett. 1986, 27, 323.
8. For synthetic spironucleosides see: a) A. Kittaka, H. Tanaka, Y. Odanaka, K. Ohnuki, K. Yamaguchi, T. Miyasaka, J. Org. Chem, 1994, 59, 3636; b) M. Yokoyama, K. Sujino, M. Irie, N. Yamazaki, T. Hiyama, N. Yamada, H. Togo, J. Chem. Soc. Perkin Trans. I 1991, 2801; c) M. Yokoyama, N. Yamada, H. Togo, Chem. Lett. 1990, 753; d) M. Yokoyama, N. Yamada, Tetrahedron Lett. 1989, 30, 3675; e) J.P. Ferris, B. Devadas, J. Org. Chem. 1987, 52, 2355; f) J.P. Ferris, B. Devadas, Tetrahedron Lett. 1986, 27, 323.
9. For synthetic spironucleosides see: a) A. Kittaka, H. Tanaka, Y. Odanaka, K. Ohnuki, K. Yamaguchi, T. Miyasaka, J. Org. Chem, 1994, 59, 3636; b) M. Yokoyama, K. Sujino, M. Irie, N. Yamazaki, T. Hiyama, N. Yamada, H. Togo, J. Chem. Soc. Perkin Trans. I 1991, 2801; c) M. Yokoyama, N. Yamada, H. Togo, Chem. Lett. 1990, 753; d) M. Yokoyama, N. Yamada, Tetrahedron Lett. 1989, 30, 3675; e) J.P. Ferris, B. Devadas, J. Org. Chem. 1987, 52, 2355; f) J.P. Ferris, B. Devadas, Tetrahedron Lett. 1986, 27, 323.
10. For synthetic spironucleosides see: a) A. Kittaka, H. Tanaka, Y. Odanaka, K. Ohnuki, K. Yamaguchi, T. Miyasaka, J. Org. Chem, 1994, 59, 3636; b) M. Yokoyama, K. Sujino, M. Irie, N. Yamazaki, T. Hiyama, N. Yamada, H. Togo, J. Chem. Soc. Perkin Trans. I 1991, 2801; c) M. Yokoyama, N. Yamada, H. Togo, Chem. Lett. 1990, 753; d) M. Yokoyama, N. Yamada, Tetrahedron Lett. 1989, 30, 3675; e) J.P. Ferris, B. Devadas, J. Org. Chem. 1987, 52, 2355; f) J.P. Ferris, B. Devadas, Tetrahedron Lett. 1986, 27, 323.
11. For synthetic spironucleosides see: a) A. Kittaka, H. Tanaka, Y. Odanaka, K. Ohnuki, K. Yamaguchi, T. Miyasaka, J. Org. Chem, 1994, 59, 3636; b) M. Yokoyama, K. Sujino, M. Irie, N. Yamazaki, T. Hiyama, N. Yamada, H. Togo, J. Chem. Soc. Perkin Trans. I 1991, 2801; c) M. Yokoyama, N. Yamada, H. Togo, Chem. Lett. 1990, 753; d) M. Yokoyama, N. Yamada, Tetrahedron Lett. 1989, 30, 3675; e) J.P. Ferris, B. Devadas, J. Org. Chem. 1987, 52, 2355; f) J.P. Ferris, B. Devadas, Tetrahedron Lett. 1986, 27, 323.
12. For synthetic spironucleosides see: a) A. Kittaka, H. Tanaka, Y. Odanaka, K. Ohnuki, K. Yamaguchi, T. Miyasaka, J. Org. Chem, 1994, 59, 3636; b) M. Yokoyama, K. Sujino, M. Irie, N. Yamazaki, T. Hiyama, N. Yamada, H. Togo, J. Chem. Soc. Perkin Trans. I 1991, 2801; c) M. Yokoyama, N. Yamada, H. Togo, Chem. Lett. 1990, 753; d) M. Yokoyama, N. Yamada, Tetrahedron Lett. 1989, 30, 3675; e) J.P. Ferris, B. Devadas, J. Org. Chem. 1987, 52, 2355; f) J.P. Ferris, B. Devadas, Tetrahedron Lett. 1986, 27, 323.
13. a) P.M. Harrington, M.E. Jung, Tetrahedron Lett. 1994, 35, 5145;
14. b) P. Chemla, Tetrahedron Lett. 1993, 34, 7391;
15. c) M. Matsumoto, M. Kirihara, T. Yoshino, T. Katoh, S. Terashima, Tetrahedron Lett. 1993, 34, 6289;
16. d) S. Mio, Y. Kumagawa, S. Sugai, Tetrahedron 1991, 47, 2133;
17. e) S. Mio, R. Ichinose, K. Goto, S. Sugai, S. Sato, Tetrahedron 1991, 47, 2111;
18. f) Ciba-Geigy, DE Pat. 41 29 728 A, 10.09.1990.
19. a) H. Sano, S. Sugai, Tetrahedron 1995, 51, 4635;
20. b) H. Sano, S. Mio, N. Tsukaguchi, S. Sugai, Tetrahedron 1995, 51, 1387;
21. c) T.W. Brandstetter, Y. Kim, J.C. Son, H.M. Taylor, P.M. Lilley, D.J. Watkin, L.N. Johnson, N.G. Oikonomakos, G.W.J. Fleet, Tetrahedron Lett. 1995, 36, 2149;
22. d) C.J.F. Bichard, E.P. Mitchell, M.R. Wormald, K.A. Watson, L.N. Johnson, S.E. Zographos, D.D. Koutra, N.G. Oikonomakos, G.W.J. Fleet, Tetrahedron Lett. 1995, 36, 2145;
23. e) H. Sano, S. Mio, J. Kitagawa, S. Sugai, Tetrahedron: Asymmetry 1994, 5, 2233;
24. f) J.W. Burton, J.C. Son, A.J. Fairbanks, S.S. Choi, H. Taylor, D.J. Watkin, B.G. Winchester, G.W.J. Fleet, Tetrahedron Lett. 1993, 34, 6119;
25. g) S. Mio, H. Sano, M. Shindou, T. Honma, S. Sugai, Agric. Biol. Chem. 1991, 55, 1105.
26. a) S. Mio, M. Ueda, M. Hamura, J. Kitagawa, S. Sugai, Tetrahedron 1991, 47, 2145;
27. b) S. Mio, M. Shiraishi, S. Sugai, H. Haruyama, S. Sato, Tetrahedron 1991, 47, 2121.
28. a) A.J. Fairbanks, G.W.J. Fleet, Tetrahedron 1995, 57, 3881;
29. b) A.J. Fairbanks, P.S. Ford, D.J. Watkin, G.W.J. Fleet, Tetrahedron Lett. 1993, 34, 3327.
30. a) J.N. BeMiller, Adv. Carbohydr. Chem. 1967, 22, 25;
31. b) D. Horton, D.H. Hutson, Adv. Carbohydr. Chem. 1963, 18, 123.
32. a) K. Utimoto, Y. Wakabayashi, T. Horiie, M. Inoue, Y. Shishiyama, M. Obayashi, H. Nozaki, Tetrahedron 1983, 39, 967;
33. b) F.G. de las Heras, P. Fernandez-Resa, J. Chem. Soc. Perkin Trans. I 1982, 903.
34. V. Uteza, G.-R. Chen, J. Le Quan Tuoi, G. Descotes, B. Fenet, A. Grouiller, Tetrahedron 1993, 49, 8579.
35. L. Somsak, G. Batta, I. Farkas, Carbohydr. Res, 1983, 124, 43.
36. a) T. Sohda, K. Mizuno, E. Imamiya, H. Tawada, K. Meguro, Y. Kawamatsu, Y. Yamamoto, Chem. Pharm. Bull. 1982, 30, 3601;
37. b) T. Sohda, K. Mizuno, E. Imamiya, Y. Sugiyama, T. Fujita, Y. Kawamatsu, Chem. Pharm. Bull. 1982, 30, 3580;
38. c) T. Sohda, K. Mizuno, H. Tawada, Y. Sugiyama, T. Fujita, Y. Kawamatsu, Chem. Pharm. Bull. 1982, 30, 3563.
39. For a review of the capto-dative effect see: H. Viehe, Z. Janousek, R. Merenyi, Acc. Chem. Res. 1985, 18, 148.
40. a) G.E. Keck, E.J. Enholm, Y.B. Yates, M.R. Wiley, Tetrahedron 1985, 41, 4079;
41. b) G.E. Keck, Y.B. Yates, J. Am. Chem. Soc. 1982, 104, 5929.
42. a) J.O. Nagy, M.D. Bednarski, Tetrahedron Lett. 1991, 32, 3953;
43. b) H. Paulsen, P. Matschulat, Liebigs Ann. Chem. 1991, 487.
44. J.N. BeMiller, M.P. Yadav, V.N. Kalabokis, R.W. Myers, Carbohydr. Res. 1990, 200, 111.