Efficient syntheses of six potentially useful optically pure macroheterocycles with ester and dihydrazide fragments were developed from available natural Δ3-carene through intermediate (31R,33S)-32,32-dimethyl-3(1,3)cyclopropyla-5-oxohexanoic acid using in the key steps [2+1]-reactions of the last with di- or triethylene glycol and [1+1]-condensation of the resulting α,ω-diketodiesters with several dicarboxylic acid dihydrazides. The structures of the obtained compounds were confirmed by IR and NMR spectroscopy and LC-MS.
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The work was performed on State Task Topic No. AAAA-A17-117011910023-2.
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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2020, pp. 419–423.
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Yakovleva, M.P., Denisova, K.S., Mingaleeva, G.R. et al. Synthesis from Δ3-Carene of Optically Active Macrolides with Fragments of Di- and Triethyleneglycol and Hydrazides of Dicarboxylic Acids. Chem Nat Compd 56, 487–491 (2020). https://doi.org/10.1007/s10600-020-03068-1
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DOI: https://doi.org/10.1007/s10600-020-03068-1