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  • Thesis

  • Authors: Wu, Tao (2006)

  • The first part of this work details the formal total synthesis of HKI 0231B and the first total synthesis of both demethyl HKI 0231A and demethyl HKI 0231B. The formal synthesis used TBAF as a mild reagent to construct the indole. The total synthesis featured an efficient radical cyclization / oxidation step to construct the skeleton and a DDQ-mediated methoxylation reaction. The second part of this work is dedicated to the synthetic efforts towards the abeo¬ergolines and the total synthesis of the abeo-ergoline analogs. In the synthetic study toward the abeo-ergolines, a reaction between 4-lithioindole and the enaminone, which was prepared from the ketone and Brederick reagent, effectively brought together all the necessary carbons for the final product. The synthesis of the abeo-...