Two ‘unnatural’ derivatives of shikimic acid, cis- and trans-6-trifluoromethylshikimic acid, have been synthesized in their racemic forms via the base-promoted opening of furan Diels–Alder adducts bearing a CF3 group. The relative stereochemistry of the trans-diastereoisomer has been confirmed by an X-ray analysis of its t-butyl ester.
J. Leroy, N. Fischer and C. Wakselman, J. Chem. Soc., Perkin Trans. 1, 1990, 1281 DOI: 10.1039/P19900001281
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