Ergot alkaloids have been of wide interest for almost a century, and new methodologies to synthesize the ergoline core are continuously being explored. We have developed a streamlined, protective group free synthesis of lysergic acid that will enable an expedient access to peptide ergot alkaloids. Key steps include a transition metal-free borrowing hydrogen reaction and an intramolecular coupling to construct the ergoline core. This sequence describes the shortest synthesis to date and allows for scaleup of tetracyclic intermediates. Lysergates, direct precursors to lysergic acid, can be telescoped and synthesized with only one chromatographic purification. Finally, during the pursuit of the total synthesis, a novel lysergate regioisomer was discovered, and a structure-activity relationship study is in progress.

Concise total synthesis of (±)-lysergic acid

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.