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Ideally oriented to complex a metal ion, the three carbonyl groups of triolide 1 are parallel and pointing in the same direction. Upon complexation with a sodium ion, the ring adjusts by arching inward, tilting the CO groups towards each other. The preparation of triolide 1 from poly(R)-3-hydroxybutanoate is surprisingly simple.
Seebàch et al. (Wed,) studied this question.