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Valuable synthetic routes to the Lycopodium alkaloid lycodine (1) and its unsymmetric dimers, complanadines A (4) and B (5), have been developed. Regioselective construction of the bicyclo[3.3.1]nonane core structure of lycodine was achieved by a remote functionality‐controlled Diels–Alder reaction and subsequent intramolecular Mizoroki–Heck reaction. A key coupling reaction of the lycodine units,...
Alkaloid Synthesis Structurally complex Lycopodium alkaloid complanadines A and B, both with unsymmetrical dimer architectures, were effectively synthesized by designing an appropriate intermediate based on C−H arylation. Our result suggests the intermediacy of a mono‐N‐oxide in the biosynthesis of dimeric alkaloids. This competent route enabled the evaluation of neuronal differentiation effects of...
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