A Concise, Enantioselective Synthesis of (+)-Decarestrictine L from Tri-O-acetyl-d-glucal

Abstract

We describe a new and efficient approach to the enantio­selective synthesis of (+)-(2R,3S,6R)-decarestrictine L from commercially available tri-O-acetyl-d-glucal, based on a stereoselective Michael addition.

Key words

Michael addition - Wolf-Kishner reaction - Wacker oxidation­

References

• 1 Grabley S. Hammann P. Huetter K. Kirsch R. Kluge H. Thiericke R. Mayer M. Zeeck A. J. Antibiot.  1992,  45:  1176 
• 2a Göhrt A. Zeeck A. Hüetter K. Kirsch R. Kluge H. Thiericke R. J. Antibiot.  1992,  45:  66 
• 2b Mayer M. Thiericke R. J. Antibiot.  1993,  46:  1372 
• 3a Machinaga N. Kibayashi C. Tetrahedron Lett.  1993,  34:  5739 
• 3b Clark JS. Whitlock GA. Tetrahedron Lett.  1994,  35:  6381 
• 3c Nokami J. Taniguchi T. Ogawa Y. Chem. Lett.  1995,  43 
• 3d Solladié G. Arce E. Bauder C. Carreño MC. J. Org. Chem.  1998,  63:  2332 
• 3e Esumi T. Kimura R. Mori M. Iwabuchi Y. Irie H. Hatakeyama S. Heterocycles  2000,  52:  525 
• 3f Lukesh JM. Donaldson WA. Tetrahedron: Asymmetry  2003,  14:  757 
• 3g García I. Gómez G. Teijeira M. Terán C. Fall Y. Tetrahedron Lett.  2006,  47:  1333 
• 3h Clark JS. Fessard TC. Whitlock GA. Tetrahedron  2006,  62:  73 
• 4 For a recent review on biological and synthetic studies on the decarestrictine family during the last fifteen years, see: Riatto VB. Pilli RA. Victor MM. Tetrahedron  2008,  64:  2279 
• 6 Mori Y. Hayashi H. J. Org. Chem.  2001,  66:  8666 
• 7a Hutchins RO. Milewski CA. Maryanoff BE. J. Am. Chem. Soc.  1973,  95:  3662 
• 7b Davies MJ. Moody CJ. J. Chem. Soc., Perkin Trans. 1  1991,  1:  9 
• 8 Marshall JA. Crooks SL. DeHoff BS. J. Org. Chem.  1988,  53:  1616 
• 9a Tsuji J. Shiizu I. Yamamoto K. Tetrahedron Lett.  1976,  34:  2975 
• 9b Clark JS. Fessard TC. Whitlock GA. Tetrahedron  2006,  62:  73 
• 10 For our preliminary results of QSAR studies on decarestrictine L, see: García I. Munteanu CR. Fall Y. Gómez G. Uriarte E. Gonzalez-Diaz H. Bioorg. Med. Chem.  2009,  17:  165 

5

Although d-glucal is commercially available, tri-O-acetyl-d-glucal is much cheaper and can be used for large-scale synthesis.