Effective syntheses of three optically active macroheterocycles with ester, azine, and dihydrazide fragments were developed from available natural L-menthol through intermediate 3R,7-dimethyl-6-oxooctanoic acid using [2 + 1]-reaction of the last with diethylene glycol and [1 + 1]-condensation of the resulting α,ω-diketodiester with hydrazine hydrate and dihydrazides of several dicarboxylic acids in the key steps. The structures of the synthesized compounds were confirmed using IR and NMR spectroscopy and GC-MS.
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The work was performed under topic No. AAAA-A17-117011910023-2 of a state task with financial support from RFBR Grant No. 17-03-01050.
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Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2018, pp. 755–757.
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Yakovleva, M.P., Mingaleeva, G.R., Denisova, K.S. et al. Synthesis of Optically Active Macrolides from L-menthol. Chem Nat Compd 54, 889–892 (2018). https://doi.org/10.1007/s10600-018-2505-x
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DOI: https://doi.org/10.1007/s10600-018-2505-x