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 (eFirst)

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.

    References

  • 1 Cron MJ. Johnson DL. Palermiti FM. Perron Y. Taylor HD. Whitehead DF. Hooper IR. J. Am. Chem. Soc.  1958,  80:  752 
  • 2 Umezawa S. Umino K. Shibahara S. Omoto S. Bull. Chem. Soc. Jpn.  1967,  40:  2419 
  • 3 Milner JL. Silo-Suh L. Lee JC. Appl. Environ. Microbiol.  1996,  62:  3061 
  • 4 Janiak AM. Milewaki S. Med. Mycol.  2001,  39:  401 
  • 5 Frost JW. Guo J. J. Am. Chem. Soc.  2002,  124:  10642 
  • 6 Arakawa K. Müller R. Mahmud T. Yu TW. Floss HG. J. Am. Chem. Soc.  2002,  124:  10644 
  • 7 Peat S. Wiggins LF. J. Chem. Soc.  1938,  1810 
  • 8 Pacak J. Trnka T. Cerny M. Coll. Czech. Chem. Commun.  1975,  40:  3038 
  • 9a Frank-Neumann M. Bissinger P. Geoffroy P. Tetrahedron Lett.  1997,  38:  4473 
  • 9b Frank-Neumann M. Bissinger P. Geoffroy P. Tetrahedron Lett.  1997,  38:  4473 
  • 9c Frank-Neumann M. Bissinger P. Geoffroy P. Tetrahedron Lett.  1997,  38:  4477 
  • 10 Frank-Neumann M. Miesch-Gross L. Gateau C. Eur. J. Org. Chem.  2000,  3693 
  • 11 Nicolaou KC. Daines RA. Chakraborty TK. Ogawa Y. J. Am. Chem. Soc.  1987,  109:  2821 
  • 12 Saito S. Nakajima H. Inaba M. Morikawe T. Tetrahedron Lett.  1989,  30:  837 
  • 13 Jurczak J. Bauer T. Chmielewski M. Carbohyd. Res.  1987,  164:  493 
  • 14 Makosza M. In Modern Synthetic Methods   Scheffold R. Schweizerischer Chemiker-Verband; Zürich: 1976.  p.7-100  
  • 15 Frank-Neumann M. Miesch-Gross L. Gateau C. Tetrahedron Lett.  1999,  40:  2829 
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.