Studies on Prostaglandins. II. Synthesis of 4-Alkoxymethyl-2-norbornen-5-one and Its Oxidation Reaction with m-Chloroperbenzoic Acid

Abstract

4-Alkoxymethyl-5-chloro-5-cyano-2-norbornene (III) was produced by the Diels-Alder reaction using 5-alkoxymethyl-cyclopentadiene and α-chloroacrylonitrile in the presence of aqueous cupric boronfluoride. III was hydrolyzed to 4-alkoxymethyl-2-norbornen-5-one (V). When V was oxidized with m-chloroperbenzoic acid, the products were varied by differences of the reaction conditions. (3β-Methoxymethyl-3α-hydroxy-4-cyclopenten-1α-yl)-acetic acid lactone (IXa) was produced by the oxidation of 4-meth-oxymethyl-2-norbornen-5-one (Va) with m-chloroperbenzoic acid in the presence of aqueous sodium bicarbonate. IXa which was very unstable was easily rearranged to 5-meth-oxymethyl-3, 3aβ, 4, 6aβ-tetrahydro-2H-cyclopenta [b] furan-2-one (Xa).