Synthesis of a conformationally restricted analogue of paclitaxel

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7177-7180

  Barboni, Luciano ^a   Lambertucci, Catia ^a   Ballini, Roberto ^a   Appendino, Giovanni ^b   Bombardelli, Ezio ^c  

^a Dipartimento di Scienze Chimiche   (Italy)

^b UNIVERSITY OF TURIN   (Italy)

^c INDENA S P A   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2',2'' METHYLENEPACLITAXEL; BACCATIN III; CARBOXYLIC ACID DERIVATIVE; CINNAMIC ACID DERIVATIVE; DIMETHYL SULFOXIDE; DOCETAXEL; DRUG ANALOG; INDENE DERIVATIVE; NATURAL PRODUCT; PACLITAXEL; PACLITAXEL DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ANISOTROPY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; DRUG CONFORMATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; ENANTIOMER; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

EID: 0032563850     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01537-8     Document Type: Article

References (30)

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24. 16. Kinetic resolution in the esterification at C-13 of protected baccatin III derivatives with both acids (Denis, J.-N.; Kanezawa, A.M.; Greene, A.E. Tetrahedron Lett. 1994, 35, 105-108) and β-lactams (Park, H.; Hepperle, M.; Boge, T.C.; Himes, R.H.; Georg, G.I. J. Med Chem. 1996, 39, 2705-2709) has been previously reported.
25. 16. Kinetic resolution in the esterification at C-13 of protected baccatin III derivatives with both acids (Denis, J.-N.; Kanezawa, A.M.; Greene, A.E. Tetrahedron Lett. 1994, 35, 105-108) and β-lactams (Park, H.; Hepperle, M.; Boge, T.C.; Himes, R.H.; Georg, G.I. J. Med Chem. 1996, 39, 2705-2709) has been previously reported.
26. -.
27. 3 (Barboni, L.; Gariboldi, P.; Appendino, G.; Enriù, R.; Gabetta, B.; Bombardelli, E. Liebigs Ann. 1995, 345-349).
28. 19. Ab initio full geometry optimisation of the C-13 side chain of 2 at Hartree-Fock level with a 6-31G (d,p) basis set gave a value of-30.3 ° for the torsion angle CHz-C-2′-C-3′-Ph. We are grateful to Dr. Marco Milanesio (Dipartimento di Chimica IFM, Università di Torino) for these calculations.
29. 50(paclitaxel): 0.67 (T28-1); 0.88 (T19-7); 1.00 (N202-1B); 1.00 (RAS+); 7.5 (MDA-MB 231).
30. 21. To address this problem, Nicolaou has suggested an alternative type of tethering, involving the 3′-phenyl and the 2-benzoate (Gomez Paloma, L.; Guy, R.K.; Wrasidlo, W.; Nicolaou, K.C. Chem. Biol. 1994, 2, 107-112). This interesting approach has not yet been implemented.