A mixture of regioisomeric 2-bromo-1-indanyl and 1-bromo-2-indanyl 2-propynyl ethers was obtained in 10.5: 1 ratio and separated by chromatography. Radical cyclization of the prevailing isomer in the presence of [chlorobis(dimethylglyoximato)(pyridine)]cobalt(III) (cobaloxime) afforded 3-methylene-tetrahydrofuran fragment; the oxidation of the latter with excess chromium(VI) oxide complex with pyridine in dichloromethane furnished a new alpha-methylene-gamma-butyrolactone in 59% yield.