Divergent and concise total syntheses of two lycopodium alkaloids, lyconadins A and C have been developed. The synthesis of lyconadin A with potent neurotrophic activity features an efficient ketal deprotective formal aza-[4+2] cyclization to form the cage-like core structure. A ketal deprotective Mannich reaction was developed to build the tricyclic structure of lyconadin C. Both lyconadins A and C were synthesized from pivotal intermediate 14. Each step to the synthesis of intermediate 14 was conducted on gram-scale.
Palladium-catalyzed synthesis of nitriles from amides has been described. Two similar, but complementary reaction conditions have been identified to convert various amides including α,β,γ,δ-unsaturated amides, cinnamides, aromatic amides and alkyl amides to the corresponding nitriles in good to excellent yield.
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