One-step synthesis of (-)-5-epi-hydantocidin

Heterocycles

Volumn 42, Issue 2, 1996, Pages 503-508

  Nakajima, Noriyuki ^a   Kirihara, Masayuki ^a   Matsumoto, Miyoko ^a   Hashimoto, Masaru ^a   Katoh, Tadashi ^a   Terashima, Shiro ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000258325     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s79     Document Type: Article

References (31)

1. M. Nakajima, K. Itoi, Y. Takamatsu, H. Okazaki, T. Kinoshita, M. Shindo, K. Kawakubo, T. Honma, M Toujigamori, and T. Haneishi, J. Antibiot., 1991, 44, 293.
2. H. Haruyama, T. Kinoshita, M. Nakajima, T. Takayama, and T. Haneishi, J. Chem. Soc., Perkin Trans. 1, 1991, 1637.
3. For the structure-activity relationships of 1: a) S. Mio, H. Sano, M. Shindo, T. Honma, and S. Sugai, Agric. Biol. Chem., 1991, 55, 1105. b) S. Mio and S. Sugai, Annu. Rep. Sankyo Res. Lab., 1991, 43, 133.
4. For the structure-activity relationships of 1: a) S. Mio, H. Sano, M. Shindo, T. Honma, and S. Sugai, Agric. Biol. Chem., 1991, 55, 1105. b) S. Mio and S. Sugai, Annu. Rep. Sankyo Res. Lab., 1991, 43, 133.
5. 4. For the total synthesis of 1: a) S. Mio, R. Ichinose, K. Goto, S. Sugai, and S. Sato, Tetrahedron, 1991, 47, 2111. b) S. Mio, Y. Kumagawa, and S. Sugai, ibid., 1991, 47, 2133. c) S. Mirza, Ger Pat. DE 4129728 A1 (1991)(Chem. Abstr., 1992, 117, 8356a). d) P. Chemla, Tetrahedron Lett., 1993, 34, 7391. e) P. M. Harrington and M. M. Jung, Tetrahedron Lett., 1994, 35, 5145.
6. For the total synthesis of 1: a) S. Mio, R. Ichinose, K. Goto, S. Sugai, and S. Sato, Tetrahedron, 1991, 47, 2111. b) S. Mio, Y. Kumagawa, and S. Sugai, ibid., 1991, 47, 2133. c) S. Mirza, Ger Pat. DE 4129728 A1 (1991)(Chem. Abstr., 1992, 117, 8356a). d) P. Chemla, Tetrahedron Lett., 1993, 34, 7391. e) P. M. Harrington and M. M. Jung, Tetrahedron Lett., 1994, 35, 5145.
7. For the total synthesis of 1: a) S. Mio, R. Ichinose, K. Goto, S. Sugai, and S. Sato, Tetrahedron, 1991, 47, 2111. b) S. Mio, Y. Kumagawa, and S. Sugai, ibid., 1991, 47, 2133. c) S. Mirza, Ger Pat. DE 4129728 A1 (1991)(Chem. Abstr., 1992, 117, 8356a). d) P. Chemla, Tetrahedron Lett., 1993, 34, 7391. e) P. M. Harrington and M. M. Jung, Tetrahedron Lett., 1994, 35, 5145.
8. For the total synthesis of 1: a) S. Mio, R. Ichinose, K. Goto, S. Sugai, and S. Sato, Tetrahedron, 1991, 47, 2111. b) S. Mio, Y. Kumagawa, and S. Sugai, ibid., 1991, 47, 2133. c) S. Mirza, Ger Pat. DE 4129728 A1 (1991)(Chem. Abstr., 1992, 117, 8356a). d) P. Chemla, Tetrahedron Lett., 1993, 34, 7391. e) P. M. Harrington and M. M. Jung, Tetrahedron Lett., 1994, 35, 5145.
9. For the total synthesis of 1: a) S. Mio, R. Ichinose, K. Goto, S. Sugai, and S. Sato, Tetrahedron, 1991, 47, 2111. b) S. Mio, Y. Kumagawa, and S. Sugai, ibid., 1991, 47, 2133. c) S. Mirza, Ger Pat. DE 4129728 A1 (1991)(Chem. Abstr., 1992, 117, 8356a). d) P. Chemla, Tetrahedron Lett., 1993, 34, 7391. e) P. M. Harrington and M. M. Jung, Tetrahedron Lett., 1994, 35, 5145.
10. For the synthesis of the epimer of 1 (2): a) A. J. Fairbanks, P. S. Ford, D. J. Watkin, and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 3327. b) A. J. Fairbanks and G. W. J. Fleet, Tetrahedron, 1995, 51, 3881.
11. For the synthesis of the epimer of 1 (2): a) A. J. Fairbanks, P. S. Ford, D. J. Watkin, and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 3327. b) A. J. Fairbanks and G. W. J. Fleet, Tetrahedron, 1995, 51, 3881.
12. For the synthesis of stereoisomers of 1: a) S. Mio, M. Shiraishi, S. Sugai, H. Haruyama, and S. Sato, Tetrahedron, 1991, 47, 2121. b) S. Mio, M. Ueda, M. Hamura, J. Kitagawa, and S. Sugai, ibid., 1991, 47, 2145.
13. For the synthesis of stereoisomers of 1: a) S. Mio, M. Shiraishi, S. Sugai, H. Haruyama, and S. Sato, Tetrahedron, 1991, 47, 2121. b) S. Mio, M. Ueda, M. Hamura, J. Kitagawa, and S. Sugai, ibid., 1991, 47, 2145.
14. For the synthesis of analogs of 1: a) J. W. Burton, J. C. Son, A. J. Fairbank, S. S. Choi, H. Taylor, D. J. Watkin, B. G. Winchester, and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 6119. b) H. Sano, S. Mio, and J. Kitagawa, Tetrahedron: Asymmetry, 1994, 5, 2233. c) A. Dondoni, M. -C. Scherrmann, A. Marra, and J. -L. Delaine, J. Org. Chem., 1994, 59, 7517. d) C. J. F. Bichard, E. P. Mitchell, M. R. Wormald, K. A. Watson, L. N. Johnson, S. P. Zographos, D. D. Koutra, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2145. e) T. W. Brandstetter, Y. -H. Kim, J. C. Son, H. M. Taylor, P. M. Q. Lilley, D. J. Watkin, L. N. Johnson, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2149. f) H. Sano, S. Mio, N. Tsukaguchi, and S. Sugai, Tetrahedron, 1995, 51, 1387. g) H. Sano and S. Sugai, Tetrahedron, 1995, 51, 4635.
15. For the synthesis of analogs of 1: a) J. W. Burton, J. C. Son, A. J. Fairbank, S. S. Choi, H. Taylor, D. J. Watkin, B. G. Winchester, and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 6119. b) H. Sano, S. Mio, and J. Kitagawa, Tetrahedron: Asymmetry, 1994, 5, 2233. c) A. Dondoni, M. -C. Scherrmann, A. Marra, and J. -L. Delaine, J. Org. Chem., 1994, 59, 7517. d) C. J. F. Bichard, E. P. Mitchell, M. R. Wormald, K. A. Watson, L. N. Johnson, S. P. Zographos, D. D. Koutra, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2145. e) T. W. Brandstetter, Y. -H. Kim, J. C. Son, H. M. Taylor, P. M. Q. Lilley, D. J. Watkin, L. N. Johnson, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2149. f) H. Sano, S. Mio, N. Tsukaguchi, and S. Sugai, Tetrahedron, 1995, 51, 1387. g) H. Sano and S. Sugai, Tetrahedron, 1995, 51, 4635.
16. For the synthesis of analogs of 1: a) J. W. Burton, J. C. Son, A. J. Fairbank, S. S. Choi, H. Taylor, D. J. Watkin, B. G. Winchester, and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 6119. b) H. Sano, S. Mio, and J. Kitagawa, Tetrahedron: Asymmetry, 1994, 5, 2233. c) A. Dondoni, M. -C. Scherrmann, A. Marra, and J. -L. Delaine, J. Org. Chem., 1994, 59, 7517. d) C. J. F. Bichard, E. P. Mitchell, M. R. Wormald, K. A. Watson, L. N. Johnson, S. P. Zographos, D. D. Koutra, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2145. e) T. W. Brandstetter, Y. -H. Kim, J. C. Son, H. M. Taylor, P. M. Q. Lilley, D. J. Watkin, L. N. Johnson, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2149. f) H. Sano, S. Mio, N. Tsukaguchi, and S. Sugai, Tetrahedron, 1995, 51, 1387. g) H. Sano and S. Sugai, Tetrahedron, 1995, 51, 4635.
17. For the synthesis of analogs of 1: a) J. W. Burton, J. C. Son, A. J. Fairbank, S. S. Choi, H. Taylor, D. J. Watkin, B. G. Winchester, and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 6119. b) H. Sano, S. Mio, and J. Kitagawa, Tetrahedron: Asymmetry, 1994, 5, 2233. c) A. Dondoni, M. -C. Scherrmann, A. Marra, and J. -L. Delaine, J. Org. Chem., 1994, 59, 7517. d) C. J. F. Bichard, E. P. Mitchell, M. R. Wormald, K. A. Watson, L. N. Johnson, S. P. Zographos, D. D. Koutra, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2145. e) T. W. Brandstetter, Y. -H. Kim, J. C. Son, H. M. Taylor, P. M. Q. Lilley, D. J. Watkin, L. N. Johnson, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2149. f) H. Sano, S. Mio, N. Tsukaguchi, and S. Sugai, Tetrahedron, 1995, 51, 1387. g) H. Sano and S. Sugai, Tetrahedron, 1995, 51, 4635.
18. For the synthesis of analogs of 1: a) J. W. Burton, J. C. Son, A. J. Fairbank, S. S. Choi, H. Taylor, D. J. Watkin, B. G. Winchester, and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 6119. b) H. Sano, S. Mio, and J. Kitagawa, Tetrahedron: Asymmetry, 1994, 5, 2233. c) A. Dondoni, M. -C. Scherrmann, A. Marra, and J. -L. Delaine, J. Org. Chem., 1994, 59, 7517. d) C. J. F. Bichard, E. P. Mitchell, M. R. Wormald, K. A. Watson, L. N. Johnson, S. P. Zographos, D. D. Koutra, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2145. e) T. W. Brandstetter, Y. -H. Kim, J. C. Son, H. M. Taylor, P. M. Q. Lilley, D. J. Watkin, L. N. Johnson, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2149. f) H. Sano, S. Mio, N. Tsukaguchi, and S. Sugai, Tetrahedron, 1995, 51, 1387. g) H. Sano and S. Sugai, Tetrahedron, 1995, 51, 4635.
19. For the synthesis of analogs of 1: a) J. W. Burton, J. C. Son, A. J. Fairbank, S. S. Choi, H. Taylor, D. J. Watkin, B. G. Winchester, and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 6119. b) H. Sano, S. Mio, and J. Kitagawa, Tetrahedron: Asymmetry, 1994, 5, 2233. c) A. Dondoni, M. -C. Scherrmann, A. Marra, and J. -L. Delaine, J. Org. Chem., 1994, 59, 7517. d) C. J. F. Bichard, E. P. Mitchell, M. R. Wormald, K. A. Watson, L. N. Johnson, S. P. Zographos, D. D. Koutra, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2145. e) T. W. Brandstetter, Y. -H. Kim, J. C. Son, H. M. Taylor, P. M. Q. Lilley, D. J. Watkin, L. N. Johnson, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2149. f) H. Sano, S. Mio, N. Tsukaguchi, and S. Sugai, Tetrahedron, 1995, 51, 1387. g) H. Sano and S. Sugai, Tetrahedron, 1995, 51, 4635.
20. For the synthesis of analogs of 1: a) J. W. Burton, J. C. Son, A. J. Fairbank, S. S. Choi, H. Taylor, D. J. Watkin, B. G. Winchester, and G. W. J. Fleet, Tetrahedron Lett., 1993, 34, 6119. b) H. Sano, S. Mio, and J. Kitagawa, Tetrahedron: Asymmetry, 1994, 5, 2233. c) A. Dondoni, M. -C. Scherrmann, A. Marra, and J. -L. Delaine, J. Org. Chem., 1994, 59, 7517. d) C. J. F. Bichard, E. P. Mitchell, M. R. Wormald, K. A. Watson, L. N. Johnson, S. P. Zographos, D. D. Koutra, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2145. e) T. W. Brandstetter, Y. -H. Kim, J. C. Son, H. M. Taylor, P. M. Q. Lilley, D. J. Watkin, L. N. Johnson, N. G. Oikonomakos, and G. W. J. Fleet, Tetrahedron Lett., 1995, 36, 2149. f) H. Sano, S. Mio, N. Tsukaguchi, and S. Sugai, Tetrahedron, 1995, 51, 1387. g) H. Sano and S. Sugai, Tetrahedron, 1995, 51, 4635.
21. M. Matsumoto, M. Kirihara, T. Yoshino, T. Katoh, and S. Terashima, Tetrahedron Lett., 1993, 34, 6289.
22. The reaction performed at 100° for 3.5 h or at 130° C for 2 h gave no trace amount of 2. The yields of 11 obtained after the prolonged reaction time at 130°C are as follows: 0.04 % (3 h), 0.07 % (4 h), 0.05 % (4.5 h).
23. 4, DBU, DMAP gave no trace amount of 2.
24. tR-2, 9.8 min.
25. All attempts to directly separate 2 from this mixture met with failure.
26. 9 345.0932; found: 345.0932.
27. 2O-Py containing DMAP (3 mol%) for 60 min at room temperature, giving 11 and the tetraaetate of 2 in 52 % and 46 % yield, respectively, after purification by column chromatography on silica gel.
28. 2O-Py in the presence of DMAP (10 mol%) at room temperature for 60 min, 12 was obtained in 89 % yield more selectively than 11.
29. T. C. Crawford and S. A. Crawford, Adv. Carbohydr. Chem. Biochem., 1980, 37, 79.
30. +-18).
31. 5