Tetrahydrofuran → HCID 5373233, compound

Participants

Reaction Steps

To 6 ml of dried tetrahydrofuran (THF) is added 321 mg of anhydrous titanium trichloride, and the mixture is stirred at room temperature in dry nitrogen atmosphere for 15 minutes while adding thereto portionwise 20 mg of lithium aluminum hydride (LAH). Thereafter, 50 mg of maytansinol is added, and the mixture is stirred at room temperature for about 30 minutes. Then, 15 ml of water is added, and the reaction mixture is extracted with chloroform, and the organic layer is washed with water and dried over anhydrous sodium sulfate. The chloroform is distilled off under reduced pressure, and the residue is purified by silica gel column chromatography [silica gel (Merck) Art 7736; solvent system: chloroform:methanol=100:1.5] to give 22 mg of 4,5-deoxymaytansinol. Yield=45.1%. Mass spectrum (m/e): 548 (M+), 530, 487.

Provenance & Evidence