Asymmetric amidation of (2S,3S)-pent-4-ene-1,2,3-triol. Total syntheses of (-)-anisomycin and (+)-polyoxamic acid

Chemical Communications

Volumn , Issue 13, 1996, Pages 1521-1522

  Kang, Sung Ho ^a   Choi, Hyeong Wook ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002895663     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001521     Document Type: Article

References (30)

1. G. Cardillo and M. Orena, Tetrahedron, 1990, 46, 3321.
2. (a) M. Tokuda, H. Fujita, T. Miyamoto and H. Suginome, Tetrahedron, 1993, 49, 2413;
3. (b) R. Ballini, E. Marcantoni and M. Petrini, J. Org. Chem., 1992, 57, 1316;
4. (c) H. Takahata, Y. Banba, M. Tajima and T. Momose, J. Org. Chem., 1991, 56, 240;
5. (d) S. Takano, Y. Iwabuchi and K. Ogasawara, Heterocycles, 1989, 29, 1861;
6. (e) H. H., Baer and M. Zamkanei, J. Org. Chem., 1988, 53, 4786;
7. (f) S. Jegham and B. C. Das, Tetrahedron Lett., 1988, 29, 4419;
8. (g) A. I. Meyer and B. Dupre, Heterocycles, 1987, 25, 113;
9. (h) H. Iida, N. Yamazaki and C. Kibayashi, J. Org. Chem., 1986, 51, 1069;
10. (i) J. G. Buchanan, K. A. MacLean and R. H. Wightman, J. Chem. Soc., Perkin Trans. 1, 1985, 1463.
11. (a) N. Chida, K. Koizumi, Y. Kitada, C. Yokoyama and S. Ogawa, J. Chem. Soc., Chem. Commun., 1994, 111;
12. (b) R. F. W. Jackson, N. J. Palmer and M. J. Wythes, J. Chem. Soc., Chem. Commun., 1994, 95;
13. (c) B. K. Banik, M. S. Manhas and A. K. Bose, J. Org. Chem., 1993, 58, 307;
14. (d) A. Dureault, F. Carreaux and J. C. Depezay, Synthesis, 1991, 151;
15. (e) I. Savage and E. J. Thomas, J. Chem. Soc., Chem. Commun., 1989, 717;
16. (f) P. Garner and J. M. Park, J. Org. Chem., 1988, 53, 2979;
17. (g) M. Hirama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29, 3125;
18. (h) A. K. Saksena, B. G. Lovey, V. M. Girijavallabhan, A. K. Ganguly and A. T. McPhail, J. Org. Chem., 1986, 51, 5024.
19. A. Jimenez and D. Vazquez, in Antibiotics, ed. F. E. Hahn, Springer Verlag, Berlin, 1979, pp. 1-19.
20. A. P. Grollman, J. Biol. Chem., 1967, 242, 3226.
21. T. Korzybsky, Z. Kowszyk-Gindifer and W. Kurytowicz, in Antibiotics, American Society of Microbiology, Washington DC, 1978, vol. 1, pp. 343-346.
22. K. Isono and S. Suzuki, Heterocycles, 1979, 13, 333; K. Isono, K. Asahi and S. Suzuki, J. Am. Chem. Soc., 1969, 91, 7490.
23. K. Isono and S. Suzuki, Heterocycles, 1979, 13, 333; K. Isono, K. Asahi and S. Suzuki, J. Am. Chem. Soc., 1969, 91, 7490.
24. M. Mori, K. Kakiki and T. Misato, Agric. Biol. Chem., 1974, 38, 699.
25. J. M. Becker, N. L. Covert, P. S. Shenbagamurthi, A. Steinfeld and F. Naider, Antimicrob. Agents Chemother., 1983, 23, 926.
26. A. J. Mancuso and D. Swern, Synthesis, 1981, 165.
27. A. Bongini, G. Cardillo, M. Orena, S. Sandri and C. Tomasini, J. Org. Chem., 1986, 51, 4905.
28. O. Mitsunobu, Synthesis, 1981, 1.
29. T. Ishizuka and T. Kunieda, Tetrahedron Lett., 1987, 28, 4185.
30. A. Abiko, J. C. Roberts, T. Takemasa and S. Masamune, Tetrahedron Lett., 1986, 27, 4537.