Ergot alkaloids. Synthesis of 6-alkyl-8-ergolenes and 6-methyl-8-aminoergolines as potential prolactin inhibitors

Abstract

The synthesis of several N-6 derivatives of elymoclavine [from Claviceps] and potential alkylating derivatives of 6-methyl-8-aminoergolines is described. These compounds were screened for prolactin-inhibiting ability [in rats], and 6-propyl-8-hydroxymethyl-8-ergolene apparently was as active as the most potent prolactin inhibitors reported to date. The total synthesis of racemic methyl dihydrolysergate I having a trans C,D ring fusion, from a tricyclic ketone is described.