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Published on: March 8, 2024
A Concise and Divergent Approach to the Naturally Occurring Tetracyclic Clavine Alkaloids (+)-Lysergol,
Alessio Regni1, Francesca Bartoccini1, Giovanni Piersanti1
1Department of Biomolecular Sciences, University of Urbino Carlo Bo, via Ca' Le Suore 2, Urbino PU-61029, Italy.
Abstract:
A concise and divergent asymmetric synthesis of the tetracyclic clavine alkaloids (+)-lysergol, (+) lysergine, and (+)-isolysergine has been accomplished using a novel strategy involving a chemoselective MeOH-mediated oxa-Michael addition and lactone-lactam rearrangement of appropriately functionalized spiro α-methylene-γ-butyrolactones, efficiently prepared from (R)-4-amino-Uhle's ketone and bromomethyl acrylate. The straightforward downstream modifications complement and expand upon previous asymmetric total syntheses of these natural products.
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