| Abstract
| - A concise, highly efficient formal total synthesis of dl-physostigmine is described, using a relativelysimple method that should be adaptable to the synthesis of homologous members of this type ofalkaloid. The key step in the synthesis is a new vicarious nucleophilic substitution reaction betweenp-nitroanisole and a C-silylated derivative of N-methylpyrrolidinone. Subsequent conversion of theinitial adduct to the tricyclic framework of physostigmine follows a well-established protocol andprovides the key intermediate 8 in high yield. The vicarious nucleophilic substitution reaction hasalso been extended to six-membered lactams, with encouraging results.
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