Synthesis of novel calystegine analogs

ORGN 924

Birgit Groetzl, bg40@le.ac.uk, Sandeep Handa, sh78@le.ac.uk, and John R. Malpass, jrm@le.ac.uk. Department of Chemistry, University of Leicester, University Road, Leicester, LE1 7RH, United Kingdom
Calystegines (polyhydroxylated nortropanes) are a class of compounds only recently discovered by Tepfer et al. The compounds are selective glycosidase inhibitors and have similar activity as swainsonine and castanospermine. To date the majority of published syntheses have focused on the preparation of naturally occurring calystegines. In this contribution we will discuss our latest results on the synthesis of non-natural calystegine analogues employing a dihydroxylation approach. Our results concerning the stereoselectivity of dihydroxylation of 7- and 8-membered and bicyclic systems will be presented.