Synthesis of paclitaxel from baccatin III by protection of the 7

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549511, C07D30514

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active

060205075

ABSTRACT:
Process for synthesizing paclitaxel by treating baccatin III with a strong base in a solvent, adding an electrophile to the solution to form a 7-O-protected baccatin III derivative, reacting the 7-O-protected baccatin III derivative with a protected paclitaxel sidechain in a solvent such that the protected paclitaxel sidechain is coupled to the 13-hydroxyl of the 7-O-protected baccatin III, and subsequently deprotecting the protected paclitaxel sidechain and the 7-O protecting group to form paclitaxel, and intermediates used therein.

REFERENCES:
patent: 5274124 (1993-12-01), Holton
patent: 5399726 (1995-03-01), Holton et al
patent: 5739362 (1998-04-01), Holton et al.
patent: 5770745 (1998-06-01), Swindell et al.
Kingston, D.G.I. et al, "Synthesis of Taxol from Baccatin III via an Oxazoline Intermediate", Tetrahedron Letters, vol. 35, No. 26, pp. 4483-4484, 1994.
Denis, J.N. et al, "A Highly Efficient, Practical Approach to Natural Taxol", J. Am. Chem. Soc., 1988, 110, 5917-5919.
Houlihan F. et al, "Phae transfer catalysis in the tert-butyloxycarbonylation of alcohols, phenols, enols, and thiols with di-tert-butyl dicarbonate", Can. J. Chem. vol. 63, pp. 153-162, 1985.
Nicolaou, K.C. et al, "Chemistry and Biology of Taxol" Angew. Chem. Int. Ed. Engl., 1994, 33, pp. 15-44.
Dasgupta et al, J. Med. Chem., vol. 37, No. 18, pp. 2976-2980, 1994.

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