Synthesis of Benzo[<i>c</i>]phenanthridine Alkaloids by Pd(OAc)₂‐Induced Direct Aromatic Carbonylation

Abstract

Abstract The Pd(OAc) 2 ‐induced carbonylation of alkoxy‐substituted 1‐amino‐2‐phenyltetralins and 1‐amino‐2‐phenylnaphthalenes was examined to provide the benzo[ c ]phenanthridine ring system. The carbonylation of substrates containing methylenedioxy groups gave oxysanguinarine and oxyavicine. The tetramethoxy derivatives gave O ‐methyloxyfagaronine. The substrate with a benzyloxy group afforded a known synthetic precursor to the antileukemic alkaloid, fagaronine.