Hydrochloric Acid → HCID 53232570, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of iron(III) oxalate hexahydrate (280.3 mg, 0.58 mmol, 30 equiv) in H2O (77 mL) was cooled to 0° C. and air was bubbled through the mixture for 10 minutes. A solution of 10′-thiomethylanhydro-vinblastine (20a, 16.2 mg, 0.019 mmol) in H2O (0.5 mL), aqueous 0.1 N HCl (0.5 mL), and CF3CH2OH (0.1 mL) was transferred by pipette to the mixture and NaBH4 (14.6 mg, 0.39 mmol, 1 equiv) in H2O (1 mL) was added to the mixture at 0° C. The resulting mixture was stirred for 30 minutes before being quenched by addition of 28-30% aqueous NH4OH (10 mL). The mixture was extracted with 10% MeOH in CH2Cl2 and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. PTLC (SiO2, Et3N:MeOH:FtOAc=3:3:97) provided 10′-thiomethylvinblastine (20b, 5.1 mg, 0.0060 mmol, 31%) as a white solid and 10′-thiomethylleurosidine (2.5 mg, 0.0029 mmol, 15%).

Provenance & Evidence