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A concise, practical approach to substituted [3.3.1]-AE-bicyclic analogs of methyllycaconitine (MLA) has been developed employing dianion alkylation and double Mannich reactions. Acetylide anion addition to substituted cyclohexanones and manipulation of the acetylide alkoxide dianion generates useful bis-propargyl tertiary alcohols. The design and synthesis of probes for nicotinic acetylcholine receptors (nAChR) affords possible leads for pesticides. MLA also has potential in probing neuronal nAChR which are implicated in some mechanisms of neurodegeneration.


Journal article


ACS Symposium Series

Publication Date





194 - 205