Preparation of 3,6-di-O-benzylallosamizoline from natural allosamidin

Tetrahedron Asymmetry

Volumn 11, Issue 10, 2000, Pages 2083-2091

  Wakabayashi, Takanori ^a   Saito, Hironao ^a   Shiozaki, Masao ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3,6 DI O BENZYLALLOSAMIZOLINE; ALLOSAMIDIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SYNTHESIS; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; FERMENTATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES;

EID: 0034595632     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00156-7     Document Type: Article

References (28)

1. (a) Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A.; Koseki, K. Tetrahedron Lett. 1986, 27, 2475-2478.
2. (b) Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A. J. Antibiotics 1987, 40, 296-300.
3. (c) Koga, D.; Isogai, A.; Sakuda, S.; Matsumoto, S.; Suzuki, A.; Kimura, S.; Ide, A. Agric. Biol. Chem. 1987, 51, 471-476.
4. (d) Sakuda, S.; Isogai, A.; Makita, T.; Matsumoto, S.; Koseki, K.; Kodama, H.; Suzuki, A. Agric. Biol. Chem. 1987, 51, 3251-3259.
5. (e) Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A.; Koseki, K.; Kodama, H.; Yamada, Y. Agric. Biol. Chem. 1988, 52, 1615-1617.
6. (f) cf. Nishimoto, Y.; Sakuda, S.; Takayama, S.; Yamada, Y. J. Antibiotics 1991, 44, 716-722.
7. (a) Trost, B. M.; van Vranken, D. L. J. Am. Chem. Soc. 1990, 112, 1261-1263.
8. (b) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1991, 32, 5123-5126.
9. (c) Nakata, M.; Akazawa, S.; Kitamura, S.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 5363-5366.
10. (d) Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 5863-5864.
11. (e) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; van Vranken, D. L. J. Chem. Soc., Chem. Commun. 1991, 1099-1101.
12. (f) Maloisel, J.-L.; Vasella, A. Helv. Chim. Acta 1992, 75, 1491-1514.
13. (g) Maloisel, J.-L.; Vasella, A.; Trost, B. M.; van Vranken, D. L. Helv. Chim. Acta 1992, 75, 1515-1526.
14. (h) Simpkins, N. S.; Stokes, S.; Whittle, A. J. J. Chem. Soc., Perkin Trans. 1 1992, 2471-2477.
15. (i) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1992, 33, 7565-7568.
16. (j) Trost, B. M.; van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444-458.
17. (k) Kitahara, T.; Suzuki, N.; Koseki, K.; Mori, K. Biosci. Biotech. Biochem. 1993, 57, 1906-1909.
18. (l) Terayama, H.; Kuzuhara, H.; Takahashi, S.; Sakuda, S.; Yamada, Y. Biosci. Biotech. Biochem. 1993, 57, 2067-2069.
19. (m) Takahashi, S.; Terayama, H.; Kuzuhara, H. Tetrahedron Lett. 1994, 35, 4149-4152.
20. (n) Goering, B. K.; Ganem, B. Tetrahedron Lett. 1994, 35, 6997-7000.
21. (o) Blattner, R.; Furneaux, R. H.; Kemmitt, T.; Tyler, P. C.; Ferrier, R. J.; Tiden, A.-K. J. Chem. Soc., Perkin Trans. 1 1994, 3411-3421.
22. (p) Takahashi, S.; Terayama, H.; Kuzuhara, H.; Sakuda, S.; Yamada, Y. Biosci. Biotech. Biochem. 1994, 58, 2301-2302.
23. (q) Blattner, R.; Furneaux, R. H.; Lynch, G. P. Carbohydr. Res. 1996, 294, 29-40.
24. (r) Shrader, W. D.; Imperiali, B. Tetrahedron Lett. 1996, 37, 599-602.
25. (s) Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9526-9538.
26. (t) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779-844.
27. Suzuki, A.; Isogai, A. Japan Kokai Tokkyo Koho, JP 07002807, 1995, 75-82 (in Japanese).
28. The numbering of allosamizoline in the nomenclature is different from that of 2H-cyclopentoxazole or 4H-cyclopentoxazole.