A short, efficient route to a protected daunosamine from L-rhamnose

Abstract

The imidate ester obtained from the reaction of methyl 2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside with trichloroacetonitrile undergoes iodonium ion-induced cyclisation, and the dihydroxazole product is subjected to reductive dehalogenation to give a protected from of daunosamine.