Cularine and Related Compounds. V. Investigation of the Ullmann Reaction Products of Methyl (2-Bromo-4, 5-dimethoxyphenyl) acetate with Phenolic Compounds, and an Approach to the Total Synthesis of Cularine.

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Preparation of the cyclic amide (II) as the key intermediate for the synthesis of cularine was elaborated. Bischler-Napieralski cyclization of this amide appeared to proceed as expected to give the desired isoquinoline derivative, didehydronorcularine, in a crude state, which, however, was readily oxidized and turned during purification into the corresponding ketone derivative, which was characterized as its picrate.