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Labeling used for nuclear magnetic resonance assignment  

Labeling used for nuclear magnetic resonance assignment  

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The macrocyclisation of hydroxyethylfuranyl acetic acid and of dehydrogenated model compounds of nonactic acid was investigated to develop a facile synthesis of nonactin analogues. By applying the Yamagushi macrocyclisation to our ω-hydroxyacids, we were able to isolate a mixture of di-, tri-, tetra- and pentameric macrocycles. Graphical abstract

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Article
Macrotetrolide α (1), a designed polynactin analog composed of (+)- and (−)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey–Mukaiyama–Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners.