Add time:09/09/2019         Source:sciencedirect.com

The α, α′-annelation of the enamine of 1,3-dihydro-2-phenalenone with methyl α-(bromomethyl)acrylate affords an aromatic bicyclic framework, methyl 8,9,10,11-tetrahydro-7,11-methano-12-keto-7H-cycloocta(de)-naphthalene-9-endo-carboxylate having the ester function positioned over the aromatic ring. The 9-exo-methyl-12, 12-dimethoxy ketal carboxylate anion derivative reacts with excess Br2 in aqueous solution affording the bromo lactone epoxide derived through capture of the intermediate of electorphilic attack on the naphthalene ring, 12, 12-dimethoxy-2, 3-endo-epoxy-11a-endo-hydroxy-1-exo, 4-dibromo-7, 11-methano-9-methyl-11a, 1, 2, 3, 4, 8, 9, 10, 11-octahydro-7 H-cycloocta [de] naphthalene-9-endo-carboxylic acid δ lactone.

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