Synthesis of Carbasugars Based on Ring Closing Metathesis: 2000-2006

Author(s): Joaquin Plumet, Ana M. Gomez, J. Cristobal Lopez.

Journal Name: Mini-Reviews in Organic Chemistry

Volume 4 , Issue 3 , 2007

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Abstract:

Carbasugars (a term coined for the carbocyclic analogues of carbohydrates) play a prominent role within the broad field of carbohydrate mimetics. Natural carbasugars, either as single molecules or as subunits of more complex molecules, have shown to display interesting biological activities. On the other hand, synthetic carbasugars have also shown similar biological activities. Normally, the construction of the carbocyclic framework is regarded as the key step in the synthesis of carbasugars. In this context, the use of ring closing metathesis (RCM) has proven to be of great value in recent synthetic approaches to carbasugars, owing to the discovery of easy to handle, robust, well defined, recyclable catalysts compatible with multiple functionalities. In this manuscript, we have focused on synthetic approaches to carbasugars and more complex derivatives that illustrate the usefulness of RCM reactions in the preparation of carbocyclic frameworks from sugar dienes.

Keywords: cross-metathesis, carbaarabinofuranoses, Trehazolamine, Cyclophellitol, Valienamine

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Article Details

VOLUME: 4
ISSUE: 3
Year: 2007
Page: [201 - 216]
Pages: 16
DOI: 10.2174/157019307781369931
Price: $58