Prostaglandin endoperoxides. 14. Solvent-induced fragmentation of prostaglandin endoperoxides. New aldehyde products from PGH2 and a novel intramolecular 1, 2 …

RG Salomon, DB Miller, MG Zagorski…

Index: Salomon; Miller; Zagorski; Coughlin Journal of the American Chemical Society, 1984 , vol. 106, # 20 p. 6049 - 6060

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Citation Number: 15

Abstract

Abstract: The prostaglandin (PG) endoperoxide nucleus, 2, 3-dioxabicyclo [2.2. 11 heptane, is three orders of magnitude less stable in aqueous vs. cyclohexane solution. Water-induced fragmentation of 2, 3-dioxabicyclo [2.2. llheptane-Z-dl exhibits a deuterium kinetic isotope effect kH/kD= 1.5. Although rate-determining cleavage of a CD bond occurs, deuterium is not lost to the protic solvent. Rather, the bridgehead deuterium migrates intramolecularly to ...