Abstract
The ortho-lithiation of a benzoic acid anilide followed by condensation with an aryl aldehyde gave a 3-arylphthalide. Reductive alkylation with 1-methoxy-1-trimethylsilyloxyethene gave a substituted aromatic carboxylic acid which was cyclised to an anthrone bearing a methoxycarbonyl methylene unit at C-10.
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