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Synthesis 2011(1): 161-167  
DOI: 10.1055/s-0030-1258320
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Laurence Miesch*a, Tania Welscha, Loic Toupetb
a Université de Strasbourg- Institut de Chimie - UMR 7177, Laboratoire de Chimie Organique Synthétique, 1 rue Blaise Pascal, BP 296/R8, 67008 Strasbourg cedex, France
Fax: +33(3)688517 54; e-Mail: lmiesch@unistra.fr;
b Université de Rennes 1-Institut de Physiques-IPR-UMR 6251, Bâtiment 11A, 35042 Rennes cedex, France
Further Information

Publication History

Received 22 September 2010
Publication Date:
28 October 2010 (online)

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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

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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.