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New acyclic apporach to 3-amino-2,3,6-trideoxy-<scp>L</scp>-hexoses: a stereocontrolled synthesis of N-benzoyl<scp>L</scp>-daunosamine
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1986
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N-benzoyl L-daunosamineNew Acyclic ApporachEngineeringOrganic ChemistryExclusive 1,3-Anti DiastereoselectivityO-t-butyldimethylsilyl L-lactaldehydeStereoselective SynthesisChemistryHeterocycle ChemistryPharmacologyAsymmetric CatalysisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
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.