First stereocontrolled synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragment of Nystatin A1

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5447-5452

  Solladié, Guy ^a   Wilb, Nicole ^a   Bauder, Claude ^a   Bonini, Carlo ^b   Viggiani, Licia ^b   Chiummiento, Lucia ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYRIC ACID DERIVATIVE; NYSTATIN; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; HYDROGENATION; HYDROLYSIS; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033597835     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990245y     Document Type: Article

References (27)

1. Hazen, E. L.; Brown, K. Science 1950, 112, 423.
2. Dutcher, J. D.; Walters, D. R.; Wintersteiner, O. J. Org. Chem. 1963, 28, 995.
3. Saltza, M.; Dutcher, J. D.; Reid, J.; Wintersteiner, O. J. Org. Chem. 1963, 28, 999.
4. Manwaring, D. G.; Rickard, R. W.; Golding, B. T. Tetrahedron Lett. 1969, 5319.
5. Chong, C. N.; Rickard, R. W. Tetrahedron Lett. 1970, 5145.
6. Borowski, E.; Zielinski, J.; Falkowski, L.; Ziminski, T.; Golik, J.; Kolodziejczyk, P.; Jereczek, E.; Gdulewicz, M.; Shenin, Y.; Kotienko, T. Tetrahedron Lett. 1971, 685.
7. Lancelin, J.-M.; Paquet, F.; Beau, J.-M. Tetrahedron Lett. 1988, 29, 2827.
8. Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521.
9. Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217.
10. Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517.
11. Bonini, C.; Righi, G.; Rossi, L. Tetrahedron 1992, 48, 9801.
12. Bonini, C.; Racioppi, R.; Viggiani, L., Righi, G.; Rossi, L. Tetrahedron: Asymmetry 1993, 4, 793.
13. Bonini, C.; Giugliano, A.; Racioppi, R.; Righi, G. Tetrahedron Lett. 1996, 37, 2487.
14. Schneider, C.; Rehfeuter, M. Tetrahedron Lett. 1998, 39, 9.
15. The transesterification reaction with PPL has been greatly improved with a chemical yield of 96 to 98%, manuscript in prepration.
16. (a) Dondoni, A.; Fogagnolo, M., Medici, A.; Pedrini, P. Tetrahedron Lett. 1985, 26, 5477. Dondoni, A.; Fantin, G.; Fogagnolo, M., Pedrini, P. J. Org. Chem. 1990, 55, 1439.
17. (a) Dondoni, A.; Fogagnolo, M., Medici, A.; Pedrini, P. Tetrahedron Lett. 1985, 26, 5477. Dondoni, A.; Fantin, G.; Fogagnolo, M., Pedrini, P. J. Org. Chem. 1990, 55, 1439.
18. (b) Dondoni, A.; Orduna, J.; Merino, P. Synthesis 1992, 201.
19. Solladié, G.; Almario, A. Tetrahedron: Asymmetry 1994, 5, 1717.
20. Almario, A. Thesis, Université Louis Pasteur, Strasbourg, 1994.
21. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
22. (b) Dana, G.; Danechpajouh, H. Bull. Soc. Chim. Fr. 1980, 395.
23. (a) Mori, Y.; Kuhara, M.; Takeuchi, A.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5419.
24. (b) Mori, Y.; Kuhara, M.; Takeuchi, A.; Kageyama, H.; Suzuki, M. Tetrahedron Lett. 1988, 29, 5423.
25. Evans, D. A.; Dart, M. J.; Duffy, J. L. Tetrahedron Lett. 1994, 35, 8541.
26. Bonini, C.; Esposito, V.; D'Auria, M.; Righi, G. Tetrahedron 1997, 53, 13419 and references therein.
27. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.