Stereoselective Synthesis of 3-Amino-3-deoxy-aldohexoses by Aldol Condensation of Tricarbonyliron-alpha-Aminodienone Complexes: Total Synthesis of Multiprotected Kanosamine
Résumé
An aldol reaction between the divalent tin enol ether of racemic N-Boc alpha-aminodienone-tricarbonyliron complex and multiprotected D-glyceraldehyde provided predominantly two enantiomerically pure ketol diastereoisomers. From there, multiprotected kanosamine and 3-amino-3-deoxy-D-altrose were obtained in a few high-yielding steps, namely stereoselective reduction, protection, decomplexation, and ozonolysis.