Synthesis of the [2H]-labelled urinary lignans enterolactone and enterodiol - Concepedia

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Synthesis of the [2H]-labelled urinary lignans enterolactone and enterodiol

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1985

Year

David N. Kirk, Leo M. McLaughlin, Alexander Lawson, Kenneth D.R. Setchell, Shailesh Kumar Patel

Journal of the Chemical Society Perkin Transactions 1

Bioorganic ChemistryBiochemistryNatural SciencesDiversity-oriented SynthesisUrinary LignansFuran-maleic Anhydride AdductSecondary MetaboliteOrganic ChemistryUrinary Lignans EnterolactonePharmacologySynthetic ChemistryNatural Product Synthesis

Abstract

Isotopically labelled forms of the urinary lignans (±)-trans-2,3-bis-(3-hydroxybenzyl)butan-4-olide (enterolactone) and (±)-2,3-bis-(3-hydroxybenzyl)butane-1,4-diol (enterodiol) have been synthesized from [4,4-2H2]butenolide, obtained from the furan-maleic anhydride adduct by reduction (NaBD4) and pyrolysis.