Oxidation of o-tyrosine ethyl ester 5, or preferably 2-carboethoxy-5-hydroxyindole 6 with Fremy's salt gave the p-quinoneimine 7. Michael addition of the nitroester 10 to 7 yielded the p-quinonemethine 11 which could be converted to a mixture of diastereomeric chlorides 12 and the imine 13 with the aid of N-chlorosuccinimide and either MnO_2 or DDQ. Trifluoroacetic acid treatment of 13 caused ring formation, and thermolysis of the resulting oxazolone 14 gave methoxatin triester 15 which was hydrolyzed to methoxatin 1 following a known procedure.