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A variety of lipid-soluble alkaloids have been detected in amphibian skin, which contains over 20 structural classes and over 800 alkaloids. Many of these poison-frog alkaloids are expected to show interesting biological activities such as inhibitory effects on the neuronal nicotinic acetylcholine receptors (nAChRs).
We envisioned an efficient and flexible synthesis of 5,8-disubstituted, 6,7-dehydro-5,8-disubstituted, and 5,6,8-trisubstituted indolizidines, 1,4-disubstituted quinolizidines, decahydroquinoline-type poison-frog alkaloids using a Michael-type conjugate addition reaction of an enaminoester as the key step as shown below.