%0 Journal Article %J Journal of Organic Chemistry %D 2018 %T Regioselective and stereoselective reductive aziridinium ring cleavage leading to azabicyclodecane architecture: enantioselective synthesis of (+)-subincanadine F %A Kalshetti, Manojkumar G. %A Argade, Narshinha P. %X Enantioselective synthesis of cytotoxic indole alkaloid (+)-subincanadine F was accomplished starting from the corresponding (S)-acetoxysuccinimide via aziridinium ring formation and its reductive ring expansion route. Regioselective and stereoselective reductive aziridinium carbon-nitrogen bond cleavage comprising ring expansions was a key step. The (S)-OMOM protection of the hydroxyl moiety adjacent to a benzylic carbon of an in situ formed aziridinium system was necessary for lithium borohydride-induced reductive ring expansions, and it also served as a latent source of an essential ketone carbonyl group for the generation of an alpha,beta-conjugated system. %B Journal of Organic Chemistry %V 83 %P 12164-12170 %8 OCT %G eng %N 19 %9 Article %3 Foreign %4 4.805 %R 10.1021/acs.joc.8b02113