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The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization.

ABSTRACT: The application of oxidative dimerization for the biomimetic synthesis of balsaminone A and ellagic acid is described. Balsaminone A is synthesized via the oxidative dimerization of 1,2,4-trimethoxynaphthalene under anhydrous conditions using CAN, PIDA in BF₃ ·OEt₂ or PIFA in BF₃ ·OEt₂ in 7-8% yields over 3 steps. Ellagic acid is synthesized from its biosynthetic precursor gallic acid, in 83% yield over 2 steps.

SUBMITTER: Daley SK

PROVIDER: S-EPMC7445397 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization.

Daley Sharna-Kay SK Downer-Riley Nadale N

Beilstein journal of organic chemistry 20200818

The application of oxidative dimerization for the biomimetic synthesis of balsaminone A and ellagic acid is described. Balsaminone A is synthesized via the oxidative dimerization of 1,2,4-trimethoxynaphthalene under anhydrous conditions using CAN, PIDA in BF3 ·OEt2 or PIFA in BF3 ·OEt2 in 7-8% yields over 3 steps. Ellagic acid is synthesized from its biosynthetic precursor gallic acid, in 83% yield over 2 steps. ...[more]

PMID: 32874349

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