Hydrochloric Acid → HCID 13269008, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of iron(III) oxalate hexahydrate (112.4 mg, 0.23 mmol, 10 equiv) in H2O (93 mL) was stirred for 2 hours, cooled to 0° C. and air was bubbled through the mixture for 10 minutes. A solution of 10′-iodoanhydrovinblastine (16a, 21.3 mg, 0.023 mmol, 1 equiv) 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 (17.6 mg, 0.464 mmol, 20 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:EtOAc=3:3:97) provided 10′-iodovinblastine (16b, 5.8 mg, 0.062 mmol, 27%) as a white solid and 10′-iodoleurosidine (2.3 mg, 0.0025 mmol, 11%). For 16b.

Provenance & Evidence