Cyclopentanes from N-amino-glyconolactams. A synthesis of mannostatin A

Chemical Communications

Volumn 8, Issue , 2003, Pages 952-953

  Hu, Guixian ^a   Zimmermann, Martin ^a   Ramana, Chepuri Venkata ^a   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA MANNOSIDASE; CYCLOPENTANE DERIVATIVE; GLYCOSIDASE INHIBITOR; LACTAM DERIVATIVE; LEAD ACETATE; MANNOSTATIN A; N AMINOGLYCONOLACTAM DERIVATIVE; RIBOSE; UNCLASSIFIED DRUG;

ACETYLATION; ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; ISOMERISM; OXIDATION; SYNTHESIS;

EID: 0037459992     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b301213a     Document Type: Article

References (40)

1. (a) T. Aoyagi, T. Yamamoto, K. Kojiri, H. Morishima, M. Nagai, M. Hamada, T. Takeuchi and H. Umezawa, J. Antibiot., 1989, 42, 883;
2. (b) H. Morishima, K. Kojiri, T. Yamamoto, T. Aoyagi, H. Nakamura and Y. Iitaka, J. Antibiot., 1989, 42, 1008;
3. (c) J. E. Tropea, G. P. Kaushal, I. Pastuszak, M. Aoyagi, R. J. Molyneux and A. D. Elbein, Biochemistry, 1990, 29, 10062.
4. Their chemistry has been reviewed, see: A. Berecibar, C. Grandjean and A. Siriwardena, Chem. Rev., 1999, 99, 779.
5. (a) A. D. Borthwick and K. Biggadike, Tetrahedron, 1992, 48((4)), 571;
6. (b) R. J. Ferrier and S. Middleton, Chem. Rev., 1993, 93, 2779;
7. (c) A. Martínez-Grau and J. Marco-Contelles, Chem. Soc. Rev., 1998, 27, 155;
8. (d) J. Marco-Contelles, C. Alhambra and A. Martínez-Grau, Synlett, 1998, 693;
9. (e) P. I. Dalko and P. Sinaÿ, Angew. Chem., Int. Ed., 1999, 38, 773.
10. (a) A. Vasella, G. J. Davies and M. Böhm, Curr. Opin. Chem. Biol., 2002, 6, 619;
11. (b) L. Remen and A. Vasella, Helv. Chim. Acta, 2002, 85, 1118;
12. (c) E. Lorthiois, M. Meyyappan and A. Vasella, Chem. Commun., 2000, 29, 1829;
13. (d) C. V. Ramana and A. Vasella, Helv. Chim. Acta, 2000, 83, 1599.
14. (a) S. Ogawa and Y. Yuming, J. Chem. Soc., Chem. Commun., 1991, 890;
15. (b) S. Knapp and T. G. M. Dhar, J. Org. Chem., 1991, 56, 4096;
16. (c) B. M. Trost and D. L. Van Vranken, J. Am. Chem. Soc., 1991, 113, 6317;
17. (d) S. B. King and B. Ganem, J. Am. Chem. Soc., 1991, 113, 5089;
18. (e) B. M. Trost and D. L. Van Vranken, J. Am. Chem. Soc., 1993, 115, 444;
19. (f) C. Li and P. L. Fuchs, Tetrahedron Lett., 1994, 35, 5121;
20. (g) S. B. King and B. Ganem, J. Am. Chem. Soc., 1994, 116, 562;
21. (h) S. Ogawa, H. Kimura, C. Uchida and T. Ohashi, J. Chem. Soc., Perkin Trans. 1, 1995, 1695;
22. (i) S. Ogawa and Y. Yuming, Bioorg. Med. Chem., 1995, 3, 939;
23. (j) R. Ling and P. S. Mariano, J. Org. Chem., 1998, 63, 6072.
24. For the formation of an N-aminoriburonolactam, see (a) R. R. Schmidt, K.-H. Jung and P. Hermentin, Chem. Ber., 1978, 111, 3311; (b) for leading references to the chemistry of non-carbohydrate derived N-aminolactams, see P. A. S. Smith, Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, The Benjing/Cummings Publishing, Massachusetts, 1983; (c) R. Braslau, M. O. Anderson, F. Rivera, A. Jimenez, T. Haddad and J. R. Axon, Tetrahedron, 2002, 58, 5513; (d) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 7277; (e) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 1508.
25. (a) For the formation of an N-aminoriburonolactam, see R. R. Schmidt, K.-H. Jung and P. Hermentin, Chem. Ber., 1978, 111, 3311; (b) for leading references to the chemistry of non-carbohydrate derived N-aminolactams, see P. A. S. Smith, Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, The Benjing/Cummings Publishing, Massachusetts, 1983; (c) R. Braslau, M. O. Anderson, F. Rivera, A. Jimenez, T. Haddad and J. R. Axon, Tetrahedron, 2002, 58, 5513; (d) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 7277; (e) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 1508.
26. (a) For the formation of an N-aminoriburonolactam, see R. R. Schmidt, K.-H. Jung and P. Hermentin, Chem. Ber., 1978, 111, 3311; (b) for leading references to the chemistry of non-carbohydrate derived N-aminolactams, see P. A. S. Smith, Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, The Benjing/Cummings Publishing, Massachusetts, 1983; (c) R. Braslau, M. O. Anderson, F. Rivera, A. Jimenez, T. Haddad and J. R. Axon, Tetrahedron, 2002, 58, 5513; (d) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 7277; (e) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 1508.
27. (a) For the formation of an N-aminoriburonolactam, see R. R. Schmidt, K.-H. Jung and P. Hermentin, Chem. Ber., 1978, 111, 3311; (b) for leading references to the chemistry of non-carbohydrate derived N-aminolactams, see P. A. S. Smith, Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, The Benjing/Cummings Publishing, Massachusetts, 1983; (c) R. Braslau, M. O. Anderson, F. Rivera, A. Jimenez, T. Haddad and J. R. Axon, Tetrahedron, 2002, 58, 5513; (d) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 7277; (e) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 1508.
28. (a) For the formation of an N-aminoriburonolactam, see R. R. Schmidt, K.-H. Jung and P. Hermentin, Chem. Ber., 1978, 111, 3311; (b) for leading references to the chemistry of non-carbohydrate derived N-aminolactams, see P. A. S. Smith, Derivatives of Hydrazine and Other Hydronitrogens Having N-N Bonds, The Benjing/Cummings Publishing, Massachusetts, 1983; (c) R. Braslau, M. O. Anderson, F. Rivera, A. Jimenez, T. Haddad and J. R. Axon, Tetrahedron, 2002, 58, 5513; (d) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 7277; (e) R. D. Miller, P. Gölitz, J. Janssen and J. Lemmens, J. Am. Chem. Soc., 1984, 106, 1508.
29. (a) R. Bisaz, Ph.D, ETH-Zürich, 1975;
30. (b) H. Kold, I. Lundt and C. Pedersen, Acta Chem. Scand., 1994, 48, 675.
31. G. Hu and A. Vasella, Helv. Chim. Acta, 2002, 85, 4369.
32. (a) R. S. Atkinson and B. J. Kelly, J. Chem. Soc., Chem. Commun., 1987, 1362;
33. (b) R. S. Atkinson and B. J. Kelly, J. Chem. Soc., Chem. Commun., 1989, 836;
34. (c) R. S. Atkinson, M. J. Grimshire and B. J. Kelly, Tetrahedron, 1989, 45, 1362.
35. (a) D. C. Iffland, L. Salisbury and Wm. R. Schafer, J. Am. Chem. Soc., 1961, 83, 747;
36. (b) R. W. Hoffmann and H. J. Luthardt, Tetrahedron Lett., 1966, 411;
37. (c) W. A. F. Gladstone and R. O. C. Norman, J. Chem. Soc. (C), 1966, 1531;
38. (d) R. W. Hoffmann and H. J. Luthardt, Chem. Ber., 1968, 101, 3851;
39. (e) R. W. Hoffmann and H. J. Luthardt, Chem. Ber., 1968, 101, 3861;
40. A. Stojiljkovic, N. Orbovic, S. Sredojevic and M. Lj. Mihailovic, Tetrahedron, 1970, 26, 1101.