Catalyzed asymmetric diels-alder reaction of benzoquinone. Total synthesis of (-)-ibogamine.
The Diels-Alder addition of diene 2 with benzoquinone catalyzed by (S)-BINOL-TiCl(2) 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.
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA. james.white@orst.edu
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D016227:Benzoquinones / Q000737:chemistry* / Q000378:metabolism*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D013237:Stereoisomerism
D016227:Benzoquinones; D001952:Bridged-Ring Compounds; C413805:ibogamine; C004532:quinone