One-pot three-component preparation of novel selenium-containing spiroketals

The one-pot three-component preparation of novel selenium-containing spiroketals with potential biological activity is described. When in situ prepared selenium dichloride is reacted with either propargyl or homopropargyl alcohols in the presence of acetone, two competitive reactions take place, namely 1,2-addition to the triple bond with the formation of the corresponding functionalized divinyl selenides in a completely regio- and stereospecific manner and selenylation at the α-position of the ketone, leading to the novel selenium-containing spiroketals. An alternative approach to the synthesis of the selenium-containing spiroketals with substantial increase of the chemical yield involves the reaction of alkynyl acetals with SeCl₂. The structure of (4E,11E)-4,11-bis(chloromethylene)-1,8-dioxa-5,12-diselenaspiro[6. 6]tridecane was unambiguously confirmed by X-ray analysis. These novel selenium-containing spiroketals were tested for regulation of glucose uptake in L6 myotubes.