Abstract
AbstractThe divergent synthesis of cis‐, 4a‐epi‐cis‐, 2‐epi‐cis‐, and trans‐decahydroquinoline‐type poison‐frog alkaloids was achieved from the known chiral acetate 5 using a stereoselective Michael‐type conjugate addition reaction and an intramolecular aldol‐type cyclization with epimerization. The conformational control was achieved on the basis of the A1,3 strain in the starting material and the stereoelectronic effect. More specifically, the synthesis of cis‐251 A, cis‐209 J‐1, cis‐223F‐1, 4a‐epi‐cis‐251 A, 2‐epi‐cis‐251 A, and trans‐251 A bearing a seven‐carbon chain at the α‐position of the nitrogen atom on the piperidine nucleus was also realized. These compounds are expected to show selective and potent inhibitory activities toward nicotinic acetylcholine receptors.
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