Simple and efficient hydrazinolysis of C-10 and C-13 ester functionalities of taxanes to obtain 10-DAB III

A process for producing 10-deacetyl baccatin III from an acidic biomass extract that contains as a constituent thereof at least one taxane that has an ester functionality on at least one of the C-10 and C-13 positions, comprising:

• (a) contacting the biomass extract with an appropriate solvent therefor, thereby to form an acidic solution that contains at least one taxane solute that has an ester functionality on at least one of the C-10 and C-13 positions;
• and
• (b) contacting said solution with a hydrazine hydrate, thereby to cleave the ester functionality of said taxane solute.

A process for producing 10-deacetyl baccatin III from a biomass extract derived from a plant of the genus Taxus, comprising contacting the biomass extract with a mixture of a solvent and a hydrazine hydrate, thereby to convert into 10-deacetyl baccatin III some taxanes in the biomass extract that are not 10-deacetyl baccatin III.

A process for converting a baccatin III analog having an ester functionality at the C-7 position thereof into 10-deacetyl baccatin III, comprising contacting a solution containing the baccatin III analog as a constituent thereof with a hydrazine hydrate, thereby to form 10-deacetyl baccatin III.

A process for producing 10-deacetyl baccatin III from an acidic solution containing a spectrum of taxanes, comprising contacting the acidic solution containing a spectrum of taxanes with from 0.6 mL to 4.0 mL of a hydrazine hydrate per 1 g total dissolved solids in said solution, thereby to convert into 10-deacetyl baccatin III some taxanes in said solution that are not 10-deacetyl baccatin III.

A process for producing 10-deacetyl baccatin III from a biomass extract that contains as a constituent thereof at least one taxane that has an ester functionality on at least one of the C-10 and C-13 positions, comprising:

• (a) contacting the biomass extract with an appropriate solvent therefor, thereby to form a solution that contains at least one taxane solute that has an ester functionality on at least one of the C-10 and C-13 positions;
• and
• (b) contacting said solution with from 0.6 mL to 4.0 mL of a hydrazine hydrate per 1 g total dissolved solids in said solution, thereby to cleave the ester functionality of said taxane solute.

A process for producing 10-deacetyl baccatin III from a biomass extract derived from a plant of the genus Taxus, wherein said biomass extract contains organic plant acids, comprising contacting the biomass extract with a mixture of a solvent and a hydrazine hydrate prior to any purification of said biomass extract by HPLC, thereby to convert into 10-deacetyl baccatin III some taxanes in the biomass extract that are not 10-deacetyl baccatin III.