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The structure and absolute configuration of the alkaloid isoline has been determined by showing that its acid portion, isolinecic acid, is (2S,3R,5S)-5-ethyl-2,5-dihydroxy-2,3-dimethylhexanedioic acid (1). The stereochemistry was defined by degradation of the acid to 3-methylheptane-2,5-dione (4) of known absolute configuration.
E. D. Coucourakis, C. G. Gordon-Gray and C. G. Whiteley, J. Chem. Soc., Perkin Trans. 1, 1972, 2339 DOI: 10.1039/P19720002339
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