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Synthesis of optically active macrolides bearing di- and triethylene glycol and dicarboxylic acid hydrazide moieties from (-)-α-pinene

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Abstract

Six optically active macroheterocycles bearing ester and dihydrazide moieties were synthesized from available natural (-)-α-pinene through the intermediate keto acid, (31R,33R)- 1-hydroxy-32,32-dimethyl-1,4-dioxopentaphane, using the [2+1] reaction of this keto acid with di- or triethylene glycols and the [1+1] condensation of the resulting α,ω-diketo diesters with dicarboxylic acid dihydrazides in the key steps.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Centre, Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    M. P. Yakovleva, G. R. Mingaleeva, K. S. Denisova & G. Yu. Ishmuratov

Authors
  1. M. P. Yakovleva
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  2. G. R. Mingaleeva
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  3. K. S. Denisova
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  4. G. Yu. Ishmuratov
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Corresponding author

Correspondence to M. P. Yakovleva.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1445–1450, July, 2019.

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Yakovleva, M.P., Mingaleeva, G.R., Denisova, K.S. et al. Synthesis of optically active macrolides bearing di- and triethylene glycol and dicarboxylic acid hydrazide moieties from (-)-α-pinene. Russ Chem Bull 68, 1445–1450 (2019). https://doi.org/10.1007/s11172-019-2575-3

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  • DOI: https://doi.org/10.1007/s11172-019-2575-3

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