%A Hanmo Zhang
%T Synthetic Studies of Meloscine and Related Alkaloids
%X The first section of this dissertation describes the discovery and studies of new radical desulfonylation reactions. These reactions allow convenient access to structurally diverse imines under mild conditions. We have examined several related desulfonylation reactions, and the results of this investigation support the general mechanism that we initially proposed.
The second section details the synthesis of (?)-epimeloscine, (?)-meloscine, and analogs. The invention of a novel, cascade radical annulation of divinylcyclopropanes enables expedient synthesis of (?)-epimeloscine and (?)-meloscine, and analogs. Preliminary studies on a chirality transfer approach towards (+)-meloscine are discussed. This approach delivered only moderate chirality transfer, however, a new cascade cope/ene reaction was discovered along the way.

%D 2013
%K imine-forming reaction; desulfonylation; alkaloid synthesis; cascade radical annulation; divinylcyclopropane; memory of chirality; cope/ene reaction
%I University of Pittsburgh
%L pittir17960