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The heteronuclear 2H-13C n.m.r. coupling pattern of methyl botryaloate, a relative of dihydro-botrydial, derived from [4-2H2, 4-13C]mevalonic acid, has been used distinguish between two possible pathways for a biosynthetic rearrangement; a 1:3 hydrogen shift occurs.
A. P. W. Bradshaw, J. R. Hanson, R. Nyfeler and I. H. Sadler, J. Chem. Soc., Chem. Commun., 1981, 649 DOI: 10.1039/C39810000649
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