Direct introduction of CH2OH by intermolecular trapping of CO

Article abstract of DOI:10.1016/S0040-4039(00)61627-1

Alkyl iodides are converted to the corresponding hydroxymethyl compounds in good yield by treatment with catalytic triphenylgermane-NaBH₃CN-AIBN in benzene-THF under an atmosphhere of CO at high pressure. This methodology is used for the synthesis of an analogue of the B ring of the calicheamicin oligoccharide in which the hydroxylamine at C4 is replaced by a hydroxymethyl group.