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.
D. N. Kirk, L. M. McLaughlin, A. M. Lawson, K. D. R. Setchell and S. K. Patel, J. Chem. Soc., Perkin Trans. 1, 1985, 35 DOI: 10.1039/P19850000035
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