Preparation of 10-deacetylbaccatin III and 7-protected-10-deacet

Details Preparation of 10-deacetylbaccatin III and 7-protected-10-deacet Preparation of 10-deacetylbaccatin III and 7-protected-10-deacet

1994-04-06

1995-09-12

Rotman, Alan L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549510, 549511, C07D30514

Patent

active

054497906

ABSTRACT:
The present invention relates to a process for converting purified, partially purified or crude taxane mixtures into a protected precursor of 10-deacetylbaccatin III and into 10-deacetylbaccatin III. The process comprises three steps, the first of which includes contacting a mixture containing at least one naturally occurring taxane compound having the structure (II) ##STR1## in which R.sub.1 is phenyl, ##STR2## [an ester linkage at the C-13 position] with at least one hydroxy protecting group. The second step involves cleaving the ester linkage of the protected taxane thus giving rise to a protected precursor of 10-deacetylbaccatin III, the deprotection of which leads to 10-deacetylbaccatin III.

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"Modified Taxols. 3. Preparation and Acylation of Baccatin III," by Magri, et al., J. Org. Chem. 1986, 51, 797-802.
"The Chemistry of Taxanes: Reaction of Taxol and Baccatin Derivatives with lewis Acids in Aprotic and Protic Media," by Chen, et al., Tetrahedron vol. 49, No. 14, pp. 2805-2828, 1993.

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