10-deacetylbaccatin III → Paclitaxel

Participants

Reaction Steps

The solid was chromatographed as described under Example 1 except that RPLC C8 silica (100 g) was used in methanol/water 20%. A pressure of 50 psi was used to obtain an adequate rate. One hundred fifty fractions of 10 ml were collected, while a gradient of 25, 35, 45, 55 and 65% methanol in water was being used. The fractions were monitored as before and fractions containing 10-deacetylbaccatin III (fractions 25-35), brevitaxane A (fractions 60-90), cephalomannine (fractions 120-125) and taxol (fractions 135-150) were combined separately, concentrated to dryness and recrystallized from chloroform/hexane (1:1) to give the pure compounds. 10-deacetylbaccatin III, brevitaxane A, 2.0 g (0.2% yield, based on plant material), cephalomannine, 0.03 g (0.003% yield, based on plant material) and taxol 0.1 g (0.01% yield, based on plant material).

Provenance & Evidence