Chloroform → Adriamycin aglycone

Reaktionsgleichung

[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:11]3[C:22]([OH:23])=[C:21]4[C:16]([CH2:17][C@@:18]([OH:29])([C:25]([CH2:27]Br)=[O:26])[CH2:19][C@@H:20]4[OH:24])=[C:15]([OH:30])[C:12]=3[C:13](=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:10].C(Cl)(Cl)Cl.[OH-:35].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:11]3[C:22]([OH:23])=[C:21]4[C:16]([CH2:17][C@@:18]([OH:29])([C:25]([CH2:27][OH:35])=[O:26])[CH2:19][C@@H:20]4[OH:24])=[C:15]([OH:30])[C:12]=3[C:13](=[O:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:10]

Komponenten

Versuchsvorschrift

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##