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.
M. Hirama, I. Nishizaki, T. Shigemoto and S. Itô, J. Chem. Soc., Chem. Commun., 1986, 393 DOI: 10.1039/C39860000393
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