Catalytic Asymmetric Approach to the Naturally Occurring Clavine Alkaloid (+)-Lysergine

• DOI: 10.1055/a-2385-5110
• Publication Date: 2024-08-13T23:24:45Z
• Authors: Mrinal K. Das; Kundan Shaw; Alakesh Bisai; Saikat Chaudhuri; Debabrata Mondal
• Keywords: Formal synthesis

Abstract An efficient asymmetric approach to the ergot alkaloids has been achieved via a highly regioselective Heck cyclization. Asymmetric induction of key intermediate was catalytic enantioselective α-aminoxylation catalyzed by d-proline (98% ee). Utilizing aforementioned strategy, formal total synthesis (+)-lysergine and (+)-isolysergine achieved. Importantly, an unnatural analogues (–)-lysergine (–)-isolysergine also using l-proline.