text: Indoline 9 was acetylated to N-acetyl compound 10 (acetic anhydride, pyridine) and then the veratryl group was then ring-opened with ozone in aqueous acetic acid to muconic ester 11 (made possible by the two electron-donating methoxide groups). This is an example of bioinspired synthesis already proposed by Woodward in 1948. Cleavage of the acetyl group and ester hydrolysis with HCl in methanol resulted in formation of pyridone ester 12 with additional isomerization of the exocyclic double bond to an endocyclic double bond (destroying one asymmetric center). Subsequent treatment with hydrogen iodide and red phosphorus removed the tosyl group and hydrolysed both remaining ester groups to form diacid 13. Acetylation and esterification (diazomethane) produced acetyl diester 14 which was then subjected to a Dieckman condensation with sodium methoxide in methanol to enol 15.