Oxidative Condensation of Quaternary Phenolic Bases

Abstract

Provided they contain quaternary nitrogen, simple phenolic bases can undergo oxidative condensation under conditions similar to those of biogenesis to form alkaloids of the isoquinoline series with good yields. By means of such oxidative condensations, more than sixty alkaloids of various structural types have become more easily obtainable. Of the numerous possible condensations of the intermediate mesomeric radicals only those which Iead to naturally occurring alkaloids give good yields and few by-products. The resuits suggest that oxidative condensations of quaternary bases are also involved in the biosynthesis of alkaloids in the plant cell.

Trifluoroacetyl‐Containing Scaffolds Assisted in Total Synthesis of Oxostephanine and Thailandine and Their Antimicrobial Activity

“…The formation of the C ring is an essential step in the synthesis of aporphine alkaloids. In prior studies, Franck and co-workers [10] employed phenolic oxidation of laudanosoline methiodide in an aqueous solution containing ferric chloride (FeCl 3 ) to produce a dehydrogenated product of 62 %. Estévez et al [11] utilized tributyltin hydride (Bu 3 SnH) and AIBN in an intramolecular radical cyclization reaction, resulting in the synthesis of the desired aporphine compound with a yield of 80 %.…”

“…The formation of the C ring is an essential step in the synthesis of aporphine alkaloids. In prior studies, Franck and co‐workers [10] employed phenolic oxidation of laudanosoline methiodide in an aqueous solution containing ferric chloride (FeCl 3 ) to produce a dehydrogenated product of 62 %. Estévez et al [11] .…”