Cyclization of functionalized ketene-N,S-acetals to substituted pyrroles: applications in the synthesis of marine pyrrole alkaloids

Abstract

α-Oxoketene-N,S-acetals, prepared by the reaction of alkyl glycinates with β oxodithiocarboxylates followed by alkylation, underwent cyclization in the presence of the Vilsmeier reagent to afford alkyl 3-aryl-4-formyl-5-(alkylsulfanyl)-1H-pyrrole-2 carboxylates in excellent yields. When the reaction was extended to β oxodithiocarboxylates derived from deoxyanisoin, 3,4-diarylpyrrole-2-carboxylates, the key intermediates in the synthesis of lukianol A and lamellarin Q were formed.