Stereoselective Synthesis of 3-Amino-3-deoxy-aldohexoses by Aldol Condensation of Tricarbonyliron-α-Aminodienone Complexes: Total Synthesis of Multiprotected Kanosamine

Abstract

An aldol reaction between the divalent tin enol ether of racemic N-Boc α-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.

Key words

α-aminodienone-tricarbonyliron complexes - divalent tin enol ether - aldol reactions - kanosamine - amino sugars

References

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16

Crystallographic data for compound 12 have been deposited at the Cambridge Crystallographic Data Center (deposition and no. CCDC-784216). Copies of these data can be obtained free of charge www.ccdc.cam.ac.uk/data_request/cif.

17

Crystallographic data for compound 15 have been deposited at the Cambridge Crystallographic Data Center (deposition and no. CCDC-701571). Copies of these data can be obtained free of charge www.ccdc.cam.ac.uk/data_request/cif.