Synthesis of l-ido-Configured Six- and Seven-Membered Carba-Sugars

Abstract

Ring-closing olefin metathesis has been successfully applied­ to the modular construction of l-ido-configured six- and seven-membered carba-sugars.

allylations - carbocycles - carbohydrates - metathesis - radical reactions

References

<A NAME="RT13706SS-1A">1a</A> Capila I. Linhardt RJ. Angew. Chem. Int. Ed.  2002,  41:  390 

<A NAME="RT13706SS-1B">1b</A> Fareed J. Hoppensteadt DA. Bick RL. Semin. Thromb. Hemost.  2000,  26:  5 

<A NAME="RT13706SS-1C">1c</A> Linhardt RJ. Gunay NS. Semin. Thromb. Hemost.  1999,  25:  5 

<A NAME="RT13706SS-2">2</A> Witczak ZJ. Nieforth KA. Carbohydrates in Drug Design   Marcel Dekker; New York: 1997. 

<A NAME="RT13706SS-3A">3a</A> Mallet J.-M. Esnault J. Driguez P.-A. Duchaussoy P. Sizun P. Hérault J.-P. Herbert J.-M. Petitou M. Sinaӱ P. Angew. Chem. Int. Ed.  2001,  40:  1670 

<A NAME="RT13706SS-3B">3b</A> Das SK. Mallet J.-M. Esnault J. Driguez P.-A. Duchaussoy P. Herault J.-P. Herbert J.-M. Petitou M. Sinaӱ P. Chem. Eur. J.  2001,  7:  4821 

<A NAME="RT13706SS-4A">4a</A> Ferrier RJ. J. Chem. Soc., Perkin Trans. 1  1979,  1455 

<A NAME="RT13706SS-4B">4b</A> Ogawa S. Ara M. Kondoh T. Saitoh M. Masuda R. Toyokuni T. Suami T. Bull. Chem. Soc. Jpn.  1980,  53:  1121 

<A NAME="RT13706SS-4C">4c</A> Ogawa S. Tsukiboshi Y. Iwasawa Y. Suami T. Carbohydr. Res.  1985,  136:  77 

<A NAME="RT13706SS-4D">4d</A> Blattner R. Ferrier RJ. J. Chem. Soc., Chem. Commun.  1987,  1008 

<A NAME="RT13706SS-4E">4e</A> Paulsen H. von Deyn W. Liebigs Ann. Chem.  1987,  125 

<A NAME="RT13706SS-4F">4f</A> Barton DHR. Géro SD. Cléophax J. Machado AS. Quiclet-Sire B. J. Chem. Soc., Chem. Commun.  1988,  1184 

<A NAME="RT13706SS-4G">4g</A> Marco-Contelles J. Pozuelo C. Jimeno ML. Martinez L. Martinez-Grau A. J. Org. Chem.  1992,  57:  2625 

<A NAME="RT13706SS-4H">4h</A> Dalko PI. Sinaӱ P. Angew. Chem. Int. Ed.  1999,  38:  773 

<A NAME="RT13706SS-4I">4i</A> Sollogoub M. Pearce AJ. Hérault A. Sinaӱ P. Tetrahedron: Asymmetry  2000,  11:  283 

<A NAME="RT13706SS-4J">4j</A> Trotter NS. Larsen DS. Stoodley RJ. Brooker S. Tetrahedron Lett.  2000,  41:  8957 

<A NAME="RT13706SS-5">5</A> Gurjar MK. Chaudhuri SR. Tetrahedron Lett.  2002,  43:  2435 

<A NAME="RT13706SS-6">6</A> Parolis H. Carbohydr. Res.  1983,  114:  21 

<A NAME="RT13706SS-7A">7a</A> Fürstner A. Angew. Chem. Int. Ed.  2000,  39:  3013 

<A NAME="RT13706SS-7B">7b</A> Yet L. Chem. Rev.  2000,  100:  2963 

For a latest comprehensive review on the utilization of RCM in carbohydrate chemistry, see:

<A NAME="RT13706SS-7C">7c</A> Roy R. Das SK. Chem. Commun.  2000,  519 

<A NAME="RT13706SS-8A">8a</A> Manna S. Jacques YP. Falck JR. Tetrahedron Lett.  1986,  27:  2679 

<A NAME="RT13706SS-8B">8b</A> Gurjar MK. Patil VJ. Pawar SM. Carbohydr. Res.  1987,  165:  313 

<A NAME="RT13706SS-9">9</A> Sudha AVRL. Nagarajan M. Chem. Commun.  1998,  925 

<A NAME="RT13706SS-10">10</A> Barton DHR. Géro SD. Cléophax J. Machado AS. Quiclet-Sire B. J. Chem. Soc., Chem. Commun.  1988,  1184