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 bioactive 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 involved in carbonyl groups reduction and double bond oxidation, resulted in the formation of a polyhydroxylated derivatives, differently substituted at C-3 position, with five 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.