New protecting group chemistry in the synthesis of moenomycin analogues

Tetrahedron Letters

Volumn 37, Issue 3, 1996, Pages 367-370

  Weigelt, Dirk ^a   Kraehmer, Ralf ^a   Welzel, Peter ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BAMBERMYCIN;

ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030045516     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02207-4     Document Type: Article

References (31)

1. For leading references, see Kempin, U.; Hennig, L.; Welzel, P.; Marzian, S.; Müller, D.; Fehlhaber, H.-W.; Markus, A.; van Heijenoort, Y.; van Heijenoort, J. Tetrahedron 1995, 51, 8471-8482.
2. Möller, U.; Hobert, K.; Donnerstag, A.; Wagner, P.; Müller, D.; Fehlhaber, H.-W.; Markus, A.; Welzel, P. Tetrahedron 1993, 49, 1635-1648.
3. Lüning, J.; Möller, U.; Debski, N.; Welzel, P. Tetrahedron Lett. 1993, 34, 5871-5874.
4. Heuer, M.; Hohgardt, K.; Heinemann, F.; Kühne, H.; Dietrich, W.; Grzelak, D.; Müller, D.; Welzel, P.; Markus, A.; van Heijenoort, Y.; van Heijenoort, J. Tetrahedron 1994, 50, 2029-2046.
5. For another series of moenomycin antibiotics, see Donnerstag, A.; Marzian, S.; Müller, D.; Böttger, D.; Stärk, A.; Fehlhaber, H.-W.; Markus, A.; van Heijenoort, Y., van Heijenoort, J. Tetrahedron 1995, 51, 1931-1940, and literature cited therein.
6. 3,4
7. Kitching, W.; Lewis, J.A.; Perkins, M.V.; Drew, R.; Moore, C.J.; Schurig, V.; König, W.A.; Francke, W. J. Org. Chem. 1989, 54, 3893-3902.
8. A very efficient protocol for the formation of ß-allyl glycosides: Takano, T.; Nakatsubo, F.; Murakami, K. Carbohydr. Res. 1990, 203, 341-342.
9. Excoffier, G.; Gagnaire, D.; Utille, J.-P. Carbohydr. Res. 1975, 39, 368-373
10. Schmidt, R.R.; Michel, J.; Roos, M. Liebigs Ann. Chem. 1984, 1343-1357.
11. Kobayashi, M.; Yamazaki, F.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1989, 30, 4547-4550.
12. 2, thus, the reaction conditions had to be carefully selected.
13. Only a trace of the isomeric α-alkoxy-ketone could be detected.
14. Schick, H.; Pogoda, B.; Schwarz, S. Z. Chem. 1982, 22, 185.
15. The concentration was about 0.2 M.
16. Zemplén, G.; Pacsu, E. Ber. Dtsch. Chem. Ges. 1929, 62, 1613-1614.
17. Evans, M.E. Carbohydr. Res. 1972, 21, 473-475.
18. See formula 1.
19. Review: Banoub, J.; Boullanger, D.; Lafont, D. Chem. Rev. 1992, 92, 1167-1195.
20. Nakabayashi, S.; Warren, C.D.; Jeanloz, R.W. Carbohydr. Res. 1986, 150, C7-C10.
21. Some trisacchande was also found.
22. 2
23. Peters, U.; Bankova, W.; Welzel, P. Tetrahedron 1987, 43, 3803-3816
24. Halmos, T.; Montserret, R.; Filippi, J.; Antonakis, K. Carbohydr. Res. 1987, 170, 57-69.
25. Corey, E.J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.
26. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022.
27. Bal, B.S.; Childers, Jr., W.E.; Pinnick, H.W. Tetrahedron 1981, 37, 2091-2096.
28. 4
29. 4, 3 h.
30. 2-1 4.68-4.72 (m).
31. In the case of diol 11a some methanol had to be added.