Chemistry of taxoids: One-step functionalization of the positions 1, 2, 9 and 10 from the selectively protected 5-O-cinnamoyltaxicine I

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9189-9192

  Al Mourabit, A ^a   Poujol, H ^a   Poupat, C ^a   Ahond, A ^a   Potier, P ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PACLITAXEL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030590945     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02152-1     Document Type: Article

References (14)

1. 1. Ettouati, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron, 1991, 47, 9823-9838
2. 2. Ettouati, L. Thèse de Doctorat en sciences de l'Université Paris-Sud, Orsay, 20 March 1991
3. 3. Poujol, H. Thèse de Doctorat en sciences de l'Université Paris-Sud, Orsay, 13 March 1996
4. 4. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K. J. Chem. Soc., Chem. Commun., 1994, 295-296
5. 5. Nicolaou, K. C.; Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc., 1995, 117, 2409-2420
6. 6. Angyal, S. J.; James, K. Aust. J. Chem., 1971, 24, 1219-1227
7. 7. Hosokawa, T.; Imada, Y.; Murahashi, S.I. J. Chem. Soc., Chem. Comm., 1983, 1245-1246
8. 8. Sato, K. I.; Igarashi, T.; Yanagisawa, Y.; Kawauchi, N.; Hashimoto, H.; Yoshimura, J. Chem. Lett., 1988, 1699-1702
9. 9. Deslonchamps, P.; Moreau, C. Can. J. Chem., 1975, 49, 2465-2467
10. 10. Deslonchamps, P.; Moreau, C.; Frehel, D.; Chenevert, R. Can. J. Chem., 1975, 53, 1204-1221
11. 3 (equation presented) The acetal protons were individually distinguished in proton NMR spectra for each epimer by nOe studies.
12. 2 in 92% yield.
13. 3) : 8.01 (dbr. 2H), 7.73 (m, 2H) ; 7.68 (d, 16 Hz,1H) ; 7.58 (m, 1H) ; 7.46 (m, 5H) ; 6.78 (s, 1H); 6.47 (d, 16 Hz, 1H) ; 5.66 (d,8 Hz, 1H) ; 5.34 (s ép., 1H) ; 5.28 (s, 1H) ; 4.58 (s, 1H) ; 4.12 (d, 8 Hz, 1H) ; 3.20 (d, 20 Hz, 1H) ; 2.74 (d, 20 Hz, 1H) ; 2,28 (s, 3H) ; 2.27 (s, 3H); 2.11 (m, 2H) ; 1.88 (m, 2H) ; 1.38 (s, 3H) ; 1.28 (s, 3H) ; 1.26 (s,3H).
14. 14. Griffith,W. P.; Ley, S. V. Aldrichimica Acta, 1990, 23, 13-19