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Trimethylaluminum-Triflimide Complexes for the Catalysis of Highly Hindered Diels-Alder Reactions and Their Use Towards the Enantiospecific Total Synthesis of Rhodexin A

  • Author(s): Guzaev, Mikhail
  • Advisor(s): Jung, Michael E
  • et al.

Rhodexin A is a cardiac glycoside first isolated from the leaves and roots of Rhodea Japonica in 1951, which shown potent activity against leukemia K562 cells (IC50 19 nM). A previous synthesis of rhodexin A has been accomplished by the Jung group. A novel synthetic approach, utilizing a convergent Diels Alder reaction with two optically active fragments deriving from Wieland-Miescher ketone and carvone, is reported. Additionally a novel Lewis acid system was developed and utilized during the synthesis and its further applications are described in Chapter 2.

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