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The enantioselective syntheses of 10-hydroxylycopodine, deacetylpaniculine, and paniculine have been accomplished through use of a common intermediate. Key steps in the synthetic sequence toward these lycopodium alkaloids include formation of the tricyclic core via a conformationally accelerated, intramolecular Mannich cyclization and an organocatalyzed, intramolecular Michael addition to form the C(7)-C(12) linkage.

Toward a Unified Approach for the Lycopodines: Synthesis of 10-Hydroxylycopodine, Deacetylpaniculine, and Paniculine