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Paper | Regular issue | Vol 71, No. 5, 2007, pp.1075-1094
Published online, 10th April, 2007
DOI: 10.3987/COM-07-11011
Dimerization of (+)-Lysergic Acid Esters

István Moldvai,* Eszter Gács-Baitz, Eszter Termesvári-Major, Luca Russo, Imre Pápai, Kari Rissanen, Éva Szárics, Julianna Kardos, and Csaba Szántay

*Department of Natural Organic Compounds, Institute of Bimolecular Chemistry, Chemical Research Center of the Hungarian Academy of Sciences, H-1525 Budapest, POB 17, Hungary

Abstract

Dimer isomer mixtures, characterized by a bridgehead C8-C8’ bond, (6a-7a; 6b-7b) were obtained from (+)-lysergic acid methyl or ethyl ester (1b; 1c) in a solution of methanol or ethanol. The isomers were separated, and their structures were determined by detailed NMR measurements and X-ray analysis. Density functional theory was applied to provide insight into the reaction mechanism. Based on an extended examination and the theoretical calculations, a plausible reaction sequence leading to dimers is also presented. The proposed mechanism has been verified by detecting the formation of the superoxide radical anion (O2·-).