Download PDF
Synthesis 1996; 1996(10): 1199-1202
DOI: 10.1055/s-1996-4367
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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