Process for the preparation of 9-desoxotaxol, 9-desoxobaccatin I

Details Process for the preparation of 9-desoxotaxol, 9-desoxobaccatin I Process for the preparation of 9-desoxotaxol, 9-desoxobaccatin I

1993-03-05

1999-11-23

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

059903252

ABSTRACT:
Process for the preparation of a derivative or analog of baccatin III or 10-desacetyl baccatin III having a C9 substituent other than keto in which the C9 keto substituent of taxol, a taxol analog, baccatin III or 10-desacetyl baccatin III is selectively reduced to the corresponding hydroxy group.

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patent: 4921974 (1990-05-01), Duggan
patent: 4924011 (1990-05-01), Denis et al.
patent: 4924012 (1990-05-01), Colin et al.
patent: 5175315 (1992-12-01), Holton
Kingston et al., "Progress in the Chemistry of Organic Natural Products 61," Springer-Verlag pp. 1-206 (1993).
Farina et al., The Chemistry of Taxanes: Unexpected Rearrangement of Baccatin III During Chemoselective Debenzoylation With Bu3SnOMe/LiCl, Tetrahedron Letters, vol. 33, No. 28, pp. 3979-3982 (1992).
Klein et al. "Synthesis of 9-Dihydrotaxol: A Novel Bioactive Taxane", Tetrahedron Letters, vol. 34, No. 13, pp. 2047-2050, 1993.
Miller et al., "Antileukemic Alkaloids from Taxus Wallichiana Zucc", J. Org. Chem. 1981, vol. 46, No. 7, pp. 1469-1474.
Chen et al., "Taxol Structure-Activity Relationships: Synthesis and Biological Evaluation of 2-Deoxytaxol", Tetrahedron Lett., vol. 34, No. 20, pp. 3205-3206 (1993).
Holton et al., "A Synthesis of Taxusin", JACS 110:6558 (1988).
Samaranayake et al., "Modified Taxols. 5.1 Reaction of Taxol with Electrophilic Reagents and Preparation of a Rearranged Taxol Derivative with Tubulin Assembly Activity3.", J. Org. Chem. 1991, 56, pp. 5114-5119.
Denis & Green, "A Highly Efficient, Practical Approach to Natural Taxol", JACS 110:5917-5919 (1988).

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