Enantioselective Synthesis via Allylic Sulfide Anions and Carbohydrate-Derived Chirons (Chemistry)

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The investigation objectives are: (1) the optimization of reaction parameters for the condensation of allylic sulfide anions with epoxides and subsequent conversion of the products into E,E-2,4-pentadienols; (2) Michael addition of malonates to an enone derived from D-glucose and subsequent transformations thereof; (3) the preparation of an electrophilic chiron and a nucleophilic chiron from D-arabinose; and (4) the eventual integration of these methodologies into a modular approach to the enantioselective synthesis of 15-oxomaytansinoids. A key element of this study is the training of talented undergraduate students for science, as well as, better preparing them for graduate studies in chemistry. This project will develop new synthetic methods directed at the preparation of very complex alkaloids that are of potential theoretical and medical value.