Studies concerning lysergic and dihydrolysergic acid α-hydroxyethylamides

Lysergic and dihydrolysergic acid α-hydroxyethylamides (Ia and IIa) undergo acid catalysed solvolytic substitutions at the asymmetric carbon atom in the side chain, resulting in the formation of epimeric compounds, The mutarotation of IIa has been studied, and shown to take place by any A-1 mechanism. The hemiacetalic character of the side chain hydroxyl, and other lines of evidence, confirm the structure Ia previously assigned to the metabolite of Claviceps paspali Stevens and Hall.