New acyclic apporach to 3-amino-2,3,6-trideoxy-L-hexoses: a stereocontrolled synthesis of N-benzoylL-daunosamine

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Abstract
N-Benzoyl L-daunosamine was synthesized stereoselectively starting from O-t-butyldimethylsilyl L-lactaldehyde and methyl propiolate; the crucial step, intramolecular conjugate addition of a carbamoyl amino group of methyl threo-5-carbamoyloxy-4-triethylsilyloxy-(Z)-hex-2-enoate, proceeded with exclusive 1,3-anti diastereoselectivity.

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