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Updated: Jun 13, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis of (+/-)-6-O-methyl and 7-demethylannulatomarin
1Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan. aamersaeed@yahoo.com
Abstract:
Synthesis of 6-O-methyl and 7-demethyl derivatives of annulatomarin (1) (6,8-dihydroxy-7-methoxy-3-phenyl-3,4-dihydroisocoumarin) isolated from the aerial parts of Hypericum annulatum is described. The key step involves an efficient, microwave-accelerated solvent and catalyst-free condensation of methyl benzoate with 3,4,5-trimethoxyhomophthalic acid (2) to afford 6,7,8-trimethoxy-3-phenylisocoumarin (3). Saponification of the latter to keto acid (4) followed reduction to furnish 6,7,8-trimethoxy-3-phenyl-3,4-dihydroisocoumarin (5), which was either regioselectively demethylated to ( +/- )-6-O-methylannulatomarin (6) or completely demethylated to ( +/- )-7-demethylannulatomarin (7).
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