Dimerization of (+)-lysergic acid esters

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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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·-).

Original languageEnglish
Pages (from-to)1075-1094
Number of pages20
JournalHeterocycles
Volume71
Issue number5
DOIs
Publication statusPublished - May 1 2007

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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  • Cite this

    Moldvai, I., Gács-Baitz, E., Termesvári-Major, E., Russo, L., Pápai, I., Rissanen, K., Szárics, É., Kardos, J., & Szántay, C. (2007). Dimerization of (+)-lysergic acid esters. Heterocycles, 71(5), 1075-1094. https://doi.org/10.3987/COM-07-11011