Optically active symmetric macrocyclic diesterazines and diesterdihydrazides were synthesized efficiently from the available natural monoterpene (+)-α-pinene (de 50%) using a [2+1]-reaction of 1′-[(1S,3S)-3-(2hydroxyethyl)-2,2-dimethylcyclobutyl]ethanone and glutaric and adipic acid chlorides followed by [1+1]condensation of the intermediate diketodiesters with hydrazine hydrate or glutaric acid dihydrazide.
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Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 195–198, March–April, 2011.
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Ishmuratov, G.Y., Mingaleeva, G.R., Shakhanova, O.O. et al. Synthesis from (+)-α-pinene of optically active macrocycles containing cyclobutane, ester, azine, or hydrazide groups. Chem Nat Compd 47, 210–214 (2011). https://doi.org/10.1007/s10600-011-9884-6
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DOI: https://doi.org/10.1007/s10600-011-9884-6