Stereoselective synthesis of the 3-hydroxytetrahydropyran part of mucocin, an antitumor agent, based on rearrangement-ring expansion reaction of a tetrahydrofuran derivative

Heterocycles

Volumn 53, Issue 6, 2000, Pages 1361-1370

  Takahashi, Shunya ^a   Fujisawa, Kenji ^a   Sakairi, Nobuo ^b   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; MUCOCIN; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0034211027     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-00-8865     Document Type: Article

References (25)

1. (a) T. Nakata, S. Nomura, and H. Matsukura, Tetrahedron Lett., 1996, 37, 213;
2. (b) T. Nakata, S. Nomura, H. Matsukura, and M. Morimoro, Tetrahedron Lett., 1996, 37, 217;
3. K. Nagasawa, N. Hori, K. Koshino, and T. Nakata, Heterocyles, 1999, 50, 919;
4. N. Hori, K. Nagasawa, T. Shimizu, and T. Nakata, Tetrahedron Lett., 1999, 40, 2145.
5. (a) M. Morimoro, H. Matsukura, and T. Nakata, Tetrahedron Lett., 1996, 37, 6365;
6. (b) T. Nakata, S. Nomura, and H. Matsukura, Chem. Pharm. Bull., 1996, 44, 627;
7. K. Nagasawa, N. Hori, R. Shiba, and T. Nakata, Heterocycles, 1997, 44, 105.
8. G. Shi, D. Alfonso, M. O. Fatope, L. Zeng, Z-m. Gu, G-X. Zhao, K. He, J. M. MacDougal, and J. L. McLaughlin, J. Am. Chem. Soc., 1995, 117, 10409.
9. M. T. Crimmins and S. W. Rafferty, Tetrahedron Lett., 1996, 37, 5649.
10. P. A. Evans and J. D. Roseman, Tetrahedron Lett., 1997, 38, 5249.
11. S. Takahashi and T. Nakata, Tetrahedron Lett., 1999, 40, 723.
12. P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha, and E. Keinan, J. Am. Chem. Soc., 1998, 120, 11279.
13. S. Baurle, S. Hoppen, and U. Koert, Angew. Chem., Int. Ed. Eng., 1999, 38, 1263.
14. P. A. Evans and V. S. Murthy, Tetrahedron Lett., 1999, 40, 1253.
15. S. Tipson and A. Cohen, Carbohydr. Res., 1965, 1, 338.
16. The overall yield of 11 from 3 was 30% in seven steps. Synthesis of 11 from L-glutamic acid was also reported by Koert et al. (21% overall yiled, eight steps); U. Koert, M. Stein, and K. Harms, Liebig. Ann., 1995, 1415, and references cited therein.
17. L. Born, F. Lieb, J. P. Lorentzen, H. Moeschler, M. Nonfon, R. Sollner, and D. Wendisch, Planta Med., 1990, 56, 312.
18. Y. Fujimoto, C. Murasaki, H. Shimada, S. Nishioka, K. Kakinuma, S. Singh, M. Singh, Y. K. Gupta, and M. Sahai, Chem. Pharm. Bull., 1994, 42, 1175.
19. B. Reitstoenm, L. Kilaas, and T. Anthonsen, Acta Chem. Scand., 1986, B 40, 440.
20. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, and Y. Kamiya, J. Am. Chem. Soc., 1989, 111, 4392.
21. K. Maruoka, T. Itoh, M. Sakurai, K. Nonoshita, and H. Yamamoto, J. Am. Chem. Soc., 1988, 110, 3588.
22. 2O, MeOH-THF, 0 °C, 12/13 = 57/43 (99%), (5) L-Selectride, THF, -78 °C, 12/13 = 8/92 (99%).
23. (a) T. Simizu, S. Hiranuma, and T. Nakata, Tetrahedron Lett., 1996, 37, 6145;
24. (b) T. Shimizu, T. Ohzeki, K. Hiramoto, N. Hori, and T. Nakata, Synthesis, 1999, 1373.
25. Y. Torisawa, H. Okabe, and S. Ikegami, Chem. Lett., 1984, 1555.