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. Author manuscript; available in PMC: 2016 May 24.
Published in final edited form as: Nat Chem. 2015 Jun 22;7(8):641–645. doi: 10.1038/nchem.2281

Figure 5. Epimerization of the Diels-Alder adducts may occur spontaneously.

Figure 5

a, b, Mild, spontaneous H/D exchange at C7c in dimers 7a and 7b indicates that epimerization of the configuration of C7c is facile, perhaps via intermediates like 12 and 13. c, Each enantiomer of 1a has a specific optical rotation value that is much larger than that reported for the natural sample of paracaseolide A (1a), suggesting that the natural substance is racemic in nature.