A mixture of cyclic lactones [7- (mentholactone), 14-, 21-, 28-, and 35-membered polylactones] instead of the expected [2 + 1]-condensation products was obtained from the reaction of 3R,7-dimethyl-6Shydroxyoctanoic acid, which is accessible from l-menthol, and glutaric, adipic, and bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dichlorides in Py in the presence of N,N-dimethylaminopyridine. The structures were confirmed using PMR, 13C NMR, and mass spectra.
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Acknowledgment
The work was financially supported by RFBR Grant No. 17-03-01050 “Synthesis of new macroheterocycles with ester, oxime, hydrazide, and amide fragments based on natural mono- and triterpenoids as promising biological and pharmaceutical compounds.”
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E. M. Vyrypaev is deceased.
Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2018, pp. 579–582.
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Yakovleva, M.P., Mingaleeva, G.R., Denisova, K.S. et al. Macrocyclic Lactonization of 3R,7-Dimethyl-6S-Hydroxyoctanoic Acid. Chem Nat Compd 54, 684–687 (2018). https://doi.org/10.1007/s10600-018-2446-4
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DOI: https://doi.org/10.1007/s10600-018-2446-4