Catalyzed Asymmetric Diels − Alder Reaction of Benzoquinone . Total Synthesis of ( − ) -Ibogamine †

  • White J
  • Choi Y
  • 5

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Abstract

The Diels−Alder addition of diene 2 with benzoquinone catalyzed by (S)-BINOL−TiCl2 produced cycloadduct 5 in >65% yield and 87% ee. The cycloadduct was transformed into (−)-ibogamine in nine steps (10% overall yield from benzoquinone). A model for the transition state leading to 5 is proposed.

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Authors

  • James D White

  • Younggi Choi

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