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Synthesis 1996; 1996(10): 1199-1202
DOI: 10.1055/s-1996-4367
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Regiospecific Electrocyclization of β-Arylvinyl Ketenimines. Formal Syntheses of the Alkaloid from Marine Origin Aaptamine

Pedro Molina* , Angel Vidal, Isidora Barquero
  • *Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, Campus de Espinardo, Espinardo-30071, Murcia, Spain, Fax +34(68)364149
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Publication Date:
31 December 2000 (online)

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Preparation of 6,7-dimethoxy-1-methyl-8-nitroisoquinoline and 6,7-dimethoxy-1-methylisoquinoline, used as precursors in the synthesis of the alkaloid aaptamine, is reported. The method is based on the regiospecific electrocyclization of the appropriate β-arylvinyl ketenimine available by aza-Wittig reaction of the corresponding vinyl iminophosphorane with (trimethylsilyl)ethenone.

aaptamine - formal synthesis - ketenimine - aza Wittig/electrocyclic ring closure

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