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Synlett 1995; 1995(1): 47-48
DOI: 10.1055/s-1995-4871
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New Routes to Acyliminium Ion Precursors and a Synthesis of the Nuevamine Skeleton

Harry Heaney* , Khamis F. Shuhaibar
  • *Department of Chemistry, The University of Technology, Loughborough, Leicestershire, LE11 3TU
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Publication Date:
31 December 2000 (online)

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Reactions of benzylamine and β-arylethylamine derivatives with 3-hydroxyphthalide followed by treatment with thionyl chloride and methanol or with methyl 2-formylbenzoate followed by treatment with a catalytic quantity of sodium methoxide in methanol provide high yield routes to α-methoxyisoindolones which function as precursors to synthetically useful acyliminium ions.

Ring-chain tautomerism - Aminol lactone - α-Methoxyisoindolone - Acyliminium ion - isoindoloisoquinoline - β-Carboline - titanium tetrachloride - Pyrophosphoryl chloride