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Synthesis of 30-Bromo- and 30-Azido-20-oxo-29-nor-3β,28-diacylbetulin Derivatives

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Abstract

Ozonolysis of 3β,28-diacyloxylup-20,29-enes gave 20-oxo-29-nor-3β,28-diacyloxylup-20,29-enes, which were brominated with molecular bromine in AcOH to obtain a mixture of 30-bromo- and 30-dibromo derivatives. Ozonolysis of 30-bromo-3β,28-diacylbetulin produced 29-nor-30-bromoketones, whose reaction with sodium azide afforded 29-nor-30-azidoketones of the lupane series.

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Acknowledgments

The authors are grateful to Engineer I.A. Borisova for recording the IR spectra, Leading Engineer O.A. Maiorova for recording the 1H and 13C spectra, and Scientific Researcher A. V. Kharitonova for elemental analysis.

Funding

The work was performed by State order (contract no. AAA-A18-118030790037-7).

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Authors and Affiliations

  1. Institute of Technical Chemistry, Perm Federal Research Center, Ural Branch, Russian Academy of Sciences, ul. Akademika Koroleva 3, Perm, 614013, Russia

    V. A. Glushkov, D. A. Schemyakina & N. K. Zhukova

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  1. V. A. Glushkov
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  2. D. A. Schemyakina
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  3. N. K. Zhukova
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Correspondence to V. A. Glushkov.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 11, pp. 1773–1780.

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Glushkov, V.A., Schemyakina, D.A. & Zhukova, N.K. Synthesis of 30-Bromo- and 30-Azido-20-oxo-29-nor-3β,28-diacylbetulin Derivatives. Russ J Org Chem 55, 1735–1741 (2019). https://doi.org/10.1134/S1070428019110150

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