Aryllead(IV) reagents in synthesis:: Formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate

[GRAPHICS] The reaction of lead(IV) 4-indolyl triacetate with substituted methyl 2-oxo-1-cyclohexanecarboxylates has been investigated as a route to the natural product N-methylwelsitindolinone C isothiocyanate. Reaction of lead(IV) reagent 18 with beta -ketoester 20 affords the desired coupled material in excellent yield and diastereoselectivity.