New Routes to Acyliminium Ion Precursors and a Synthesis of the Nuevamine Skeleton

(opens in new window) Buy Article (opens in new window) Permissions and Reprints (opens in new window) All articles of this category (opens in new window) 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