Studies on Practical Synthetic Methods of Pyrrolidine and Piperidine Alkaloids Utilizing Electrochemical Reactions

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The main results obtained in the research were as follow ; i) Lewis acid treatment of anodically prepared dimethyl N-methoxycarbonyl-N-methoxymethylaminomalonate with aryl olefins afforded beta -aryl- pyrrolidine derivatives, and one of the products was successfully converted to mesembrine. ii) An alkyl group was introduced to the alpha' position of alpha-substituted pyrrolidines with high diastereoselectivities by modifying the alpha'-substituents or the functional groups located at the nitrogen atom of pyrrolidine ring. iii) Optically active N-methylpsuedconhidrine was synthesized by anodic beta -acetoxylation of piperidine derivatives. iv) Regioselective alkylation on a piperidine ring was achieved by using beta, gamma-unsatureated N-alkoxycarbonylpiperidines which were prepared from N-alkoxycarbonylpiperidinesby utilizing anodic oxidation in a key step, and this reaction was applied to the synthesis of meroquinene, etc. v) Nitrogen-containing bicyclic compounds were synthesized by the reaction of alpha, alpha' -di- cation or alpha, gamma- dication equivalents with dianion equivalents. vi) Conditions for the efficient electroreductive decyanation were found and they were applied to the synthesis of alpha-substituted pyrrolidine and piperidine derivatives. vii) A new route for the generation of alpha -amino carbanions was exploited.