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Synthesis and spectroscopic studies of furan-bridged polyazamacrocycles through 15,16-bis((prop-2-ynylamino)methyl)labdatriene transformations

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Abstract

The design and the preparation of a small library of optically active polyazamacrocyclic compounds with a furan bridge, connected by (4-(methylaminomethyl)-1,2,3-triazole) rings with methylene, ethyloxyethyl or ethylethoxyethyl units from natural labdanoid lambertianic acid is reported. The synthesis of the key 15,16-bis((tert-butoxycarbonyl(prop-2-ynyl)amino)methyl)labda-8(9),13,15-labdatriene from the plant diterpenoid lambertianic acid is also described. CuAAC reaction of this compounds with various diazides in the presence of Cu(II)/sodium ascorbate in methylene chloride/water reaction medium led to the mentioned chiral macrocyclic compounds with a furan bridge binding Zn2+ ions in solution.

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Acknowledgements

This work was performed under financial support in part from the Russian Federation of Basic Research (projects No 18-03-01012) and the Russian Science Foundation and the Government of the Novosibirsk Region (research project No 17-43-543235). Authors would like to acknowledge the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements.

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Authors and Affiliations

  1. Laboratory of Medicinal Chemistry, Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentyev Avenue, 9, Novosibirsk, Russia, 630090

    Olga I. Brusentzeva, Yurii V. Kharitonov, Dmitry S. Fadeev & Elvira E. Shults

  2. Novosibirsk State University, Pirogova St. 2, Novosibirsk, Russia, 630090

    Elvira E. Shults

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  1. Olga I. Brusentzeva
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  2. Yurii V. Kharitonov
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  3. Dmitry S. Fadeev
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  4. Elvira E. Shults
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Correspondence to Elvira E. Shults.

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10847_2019_965_MOESM1_ESM.doc

Supplementary material 1—Experimental procedures, characterization data, and copies of 1H and 13C NMR spectra for new compounds (DOC 4362 kb)

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Brusentzeva, O.I., Kharitonov, Y.V., Fadeev, D.S. et al. Synthesis and spectroscopic studies of furan-bridged polyazamacrocycles through 15,16-bis((prop-2-ynylamino)methyl)labdatriene transformations. J Incl Phenom Macrocycl Chem 96, 245–250 (2020). https://doi.org/10.1007/s10847-019-00965-z

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