STEREOSELECTIVE ACCESS TO ALPHA-AZIDO ALDEHYDES AND A NEW SYNTHETIC ROUTE TO MYRIOCIN

Reaction of dichloromethyllithium with six-membered carbohydrate keton es followed by azide ion treatment furnished stereoselectively alpha-a zido aldehydes, potential intermediates in the synthesis of alpha-subs tituted alpha-amino acids. The same reaction sequence applied to an ac yclic ketone 10a allowed the preparation of an alpha-azido aldehyde 12 which could be converted in four steps into a known intermediate 14b of the total synthesis of the immunosuppressant myriocin 16.