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Synthesis 1996; 1996(10): 1199-1202
DOI: 10.1055/s-1996-4367
DOI: 10.1055/s-1996-4367
paper
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Regiospecific Electrocyclization of β-Arylvinyl Ketenimines. Formal Syntheses of the Alkaloid from Marine Origin Aaptamine
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Publication History
Publication Date:
31 December 2000 (online)
![](https://www.thieme-connect.de/media/synthesis/199610/lookinside/thumbnails/10.1055-s-1996-4367-1.jpg)
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