The hydrolytic opening of the epoxide ring of (5b) under alkaline conditions proceeds via a β-lactone according to Scheme 2; one of the methylcitric acids obtained in the citrate synthase reaction possesses the stereostructure (3) and not, as previously published, structure (2).
S. Brandänge, O. Dahlman and L. Mörch, J. Chem. Soc., Chem. Commun., 1980, 555 DOI: 10.1039/C39800000555
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