Anodic cyanation of C-4 hydroxylated piperidines: total synthesis of (±)-alkaloid 241D

A stereospecific synthesis of dendrobates (±)-alkaloid 241D is described. Key steps in this approach involved the stepwise electrochemical synthesis of C-4 substituted α-aminonitriles and their alkylation with iodomethane and 1-bromononane, respectively. The N-aryl group was removed in the last step through a Birch dearomatization followed by the hydrolysis of the intermediate dienamines.