The synthesis of new polyhydroxylated 8-oxabicyclo[3.2.1]octanes and 2,7-dioxatricyclo[4.2.1.0
3,8]nonanes is described. These structures is an interesting synthetic blocks for potential bioacti
ve molecules. The precursor, 3-chloro-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione was obtained from reaction of tetrachlorocyclopropene with furan, then it was in
vol
ved in carbonyl groups reduction and double bond oxidation, resulted in the formation of a polyhydroxylated deri
vati
ves, differently substituted at C-3 position, with fi
ve new stereocenters.
Using intramolecular transannular hydroxycyclization, bicyclic epoxy diacetate was transformed into 2,7-dioxatricyclo[4.2.1.03,8]nonane in high yield through an alkoxide intermediate. Compounds thus obtained have a structure close to certain molecules with antitumor and glycosidase inhibitors activity.