Abstract
A method improving on the Corey method of prostaglandin synthesis bypasses the need for isolating and then hydrolyzing the intermediate bicyclic lactone to obtain hydroxy acid for optical resolution. Treatment of the ketone (about 85% pure) with 1.20 equivalent of sodium hydroxide rapidly and exothermically yielded the desired product. This material could be isolated (quantitative) and resolved via d-ephedrine. Purification of this salt removed by-products formed from oxidation of undesired isomers of the starting ketone. Racemic lactone could also be produced by direct iodolactonization of the resulting basic solution. This basic hydrogen peroxide cleavage of a bicyclic ketone to form a prostaglandin intermediate greatly reduces time and cost of reagents.
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