Stereoselective synthesis of sugar mimetics from simple monosaccharides

8^th European Chemistry Congress

June 21-23, 2018 | Paris, France

Slawomir Jarosz

Institute of Organic Chemistry Polish Academy of Sciences, Poland

Keynote: Chem Sci J

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.

Biography :

Slawomir Jarosz has completed his PhD in 1979 at the IOC, PAS and he is now a full professor at this Institute since 1999. Since 2011 he is a general director of this institute and, since 1999, a head of the carbohydrate group. He spent 1 year (1980) as a post-doc in the group of professor Bert Fraser-Reid (Maryland, US) and 1 year as a visiting scientist (1988) at Duke University (US). He published ca 190 papers and promoted 18 PhD students.

E-mail: slawomir.jarosz@icho.edu.pl