Chloroform → Adriamycin aglycone

Participants

Reaction Steps

In order to introduce a hydroxyl group at the 14- position of compound (IX), said position is first provided with a bromine atom in conventional bromination step (Br2, CHCl3, 23°, 16 hrs). The 14-bromodaunomycinone (X), after being freed of CHCl3, is dissolved in aqueous acetone and subjected to hydrolysis with NaOH (1.1 eq, reflux 5 mins) to afford adriamycinone (XI) which is recovered after water workup and extraction with CHCl3 /MeOH. This portion of the process forms the subject of Example 7. ##STR4##

Provenance & Evidence