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Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII.* synthesis of ω-carboxy derivatives of 20-hydroxyecdysone diacetonide

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Abstract

Ozonolysis of ω-anhydro-20-hydroxyecdysone diacetonide gave a mixture of 24- and 25-oxo derivatives, and only the first of these (23-carbaldehyde) reacted with malonic acid according to Knoevenagel to give 14α-hydroxy-2β,3β: 20,22-bis(isopropylidenedioxy)-6-oxo-27-nor-5β-cholesta-7,24-dien-26-oic acid. The oxidation of 23-carbaldehyde with ozone, followed by treatment with diazomethane, afforded 20-hydroxy-25,26,27-trinorecdysone-23-carboxylic acid methyl ester diacetonide.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075, Bashkortostan, Russia

    R. G. Savchenko, Ya. R. Urazaeva, S. A. Kostyleva & V. N. Odinokov

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  1. R. G. Savchenko
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  2. Ya. R. Urazaeva
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  3. S. A. Kostyleva
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  4. V. N. Odinokov
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Correspondence to V. N. Odinokov.

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Original Russian Text © R.G. Savchenko, Ya.R. Urazaeva, S.A. Kostyleva, V.N. Odinokov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 4, pp. 626–628.

For communication LXVII, see [1].

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Savchenko, R.G., Urazaeva, Y.R., Kostyleva, S.A. et al. Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII.* synthesis of ω-carboxy derivatives of 20-hydroxyecdysone diacetonide. Russ J Org Chem 49, 610–613 (2013). https://doi.org/10.1134/S1070428013040192

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  • DOI: https://doi.org/10.1134/S1070428013040192

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