The total synthesis of four of the eight possible racemates having the estrone structure has been described. One of these proved to be the dl-iotm of the natural hormone, and has been resolved. Another has been identified as lumiestrone. The synthetic scheme employed is summarized below. The potassium salt of m-methoxyphenylacetylene (prepared from m-hydroxyacetophenone) was added to decalin-l,5-dione in a 1:1 molecular ratio. The acetylenic bond of the resulting 28.34

Formation and Reactions of Glycidic Esters 4995 Villa was also obtained when khellol (lb) or 2-norvisnagin (Ic) was oxidized under the same conditions.Methyl (4,6-Dimethoxybenzofuran)-5-carboxylate (Vllb).-One gram of Vila was methylated by refluxing it with 25 cc. of acetone, 3 g. of anhydrous potassium carbonate and 5 cc. of methyl iodide for 24 hours. The acetone solution was then filtered off and on its evaporation Vllb was obtained which separated from acetone in colorless crystals, m.p. 83-84°. Vllb was insoluble in alkali and gave a negative ferric chloride reaction.Anal. Caled, for C12H12O5: C, 61.0; H, 5.1. Found: C, 61.3; H, 5.2. 6-Hydroxy-4,7-dimethoxybenzofuran-5-carboxylic Acid (Vile).-When khellin (II) was oxidized with hydrogen peroxide under the same conditions as visnagin, colorless crystals of Vile were obtained, which, when crystallized from alcohol, had m.p. 149°. Vile gave a blue color with ferric chloride, and was soluble in sodium bicarbonate solution.

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