Six-Step Synthesis of (±)-Lysergic Acid
Brian J. Knight, Ryan Harbit, Joel M. Smith
Abstract
This article describes a concise synthesis of lysergic acid from simple aromatic precursors. The successful strategy relies on the coupling, dearomatization, and cyclization of a halopyridine with a 4-haloindole derivative in 6 total synthetic steps from commercial starting materials. In addition to highlighting the advantages of employing dearomative retrosynthetic analysis, the design is practical and anticipated to enable the synthesis of novel neuroactive compounds as exemplified by the synthesis of a novel natural product derivative, 12-chlorolysergic acid.
Topics & Concepts
Lysergic acidNatural productTotal synthesisDerivative (finance)Combinatorial chemistryRetrosynthetic analysisChemistryOrganic chemistryFinancial economicsEconomicsChemical synthesis and alkaloidsPlant and fungal interactionsPsychedelics and Drug Studies