Synthesis of taxol, taxol analogs and their intermediates with v

Details Synthesis of taxol, taxol analogs and their intermediates with v Synthesis of taxol, taxol analogs and their intermediates with v

1994-12-15

1998-06-23

Trinh, Ba K.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549511, C07D30514

Patent

active

057707456

ABSTRACT:
An efficient protocol for the synthesis of taxol, taxol analogs and their intermediates is described. The process incudes the attachment of the taxol A-ring side chain to baccatin III and for the synthesis of taxol and taxol analogs with variable A-ring side chain structures. A rapid and highly efficient esterification of O-protected isoserine and 3-phenylisoserine acids having N-benzyoloxycarbonyl groups to the C-13 hydroxyl of 7-O-protected baccatin III is followed by a deprotection-acylation sequence to make taxol, celphalomanninne and various analogs, including photoaffinity labeling candidates.

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"New and Efficient Approaches to the Semisynthesis of Taxol and its C-13 Side Chain Analogs by Means of B-Lactam Synthon Method", Ojima et al., Tetrahedron, vol. 48, No. 34, pp. 6985-7012, 1992.
Improved Protection and Esterification of a Precursor of the Taxotere and Taxol Side Chains, Commercon et al, Tetrahedron, vol. 33, No. 36, pp. 5185-5188, 1992.
"Highly Sterocontrolled and Efficient Preparation of the Protected Esterification-Ready Docetaxel (Taxotere) Side Chain", Kanazawa et al, Org. Chem, vol. 59, No. 6, pp. 1238-1240, 1994.

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