Synthesis of paclitaxel from baccatin III by protection of the 7-hydroxyl of baccatin III using a strong base and an electrophile
AssigneeBristol-Myers Squibb Company
InventorFrancis S. Gibson
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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.
Claims6
A process for preparing paclitaxel by converting baccatin III into 7-O-acyl-protected baccatin III in good yield and high quality with an electrophilic protecting group of the formula
- with a strong base in a solvent of the general formula, R—CONR′2, wherein
- R is alkyl, aryl, R′O—, or R′2N—, or R′S—;
- R′ is butyl or C2-3 alkenyl;
- and
- X is halogen, imidazoyl, benztriazole, N-(benzyloxycarboxyloxy) succinimide, OR′, or —OOCOR.
Dependencies are inferred from the claim text.