Slawomir Jarosz
Institute of Organic Chemistry Polish Academy of Sciences, Poland
Title: Stereoselective synthesis of sugar mimetics from simple monosaccharides
Biography
Biography: Slawomir Jarosz
Abstract
The concise approach to bicyclic imino- and carbasugars from simple monosaccharides will be presented. First method is based on the fragmentation of sugar allyltins (e.g. 5) into dienoaldehyde 1 which is further converted into carbasugars (3, 4b) or iminosugars (2, 4a. The configuration at the ring junction (cis-decalin and trans-hydrindane), is fixed which results from the mechanism of the cyclization of intermediates.Problem of obtaining the alternative trans isomers of decalin was solved by an introduction of both substituents in the trans-relation before cyclization (route b). Aldehyde 1 was also used for the preparation of iminosugars (e.g. 2 and 4a). Besides the ‘allyltin’ approach to iminosugars, we have elaborated also another one starting from sugar derived bromonitriles (e.g. 9) which allow for the efficient preparation of bicyclic iminosugars.