A facile approach to 2-alkoxyindolin-3-one and its application to the synthesis of N -benzyl matemone.

2-Alkoxycarbonylindolin-3-one is synthesized from a methoxyglycine derivative via a 1,2-aza-Brook rearrangement followed by cyclization with bis(trimethylsilyl)aluminum chloride. A short-step synthesis of N -benzyl matemone is successfully carried out using the present indolin-3-one synthesis.