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Synthesis and spectroscopic studies of chiral macrocyclic furanolabdanoids connected on the 16,17-positions by 1,2,3-triazole rings with methylene or oxamethylene units

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Abstract

Derivatives of natural diterpenoid methyl lambertianate containing propargyloxy substituents in 16,17-positions were obtained. CuAAC reaction of methyl 17-propargyloxy-16-[(prop-2-yn-1-yloxy)methyl]labdadienoate with various diazides in the presence of Cu(II)/sodium ascorbate in methylene chloride/water reaction medium gave chiral macrocyclic compounds connected on the 16 and 17-positions by 1,2,3-triazole rings with methylene, ethyloxyethyl or ethylethoxyethyl units. The obtained macrocyclic structures showed high selectivity and affinity for Hg2+ ion by the 1,2,3-triazole rings.

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Acknowledgments

This work was performed under financial support in part from the Russian Science Foundation (Grant 14-13-00822) and the Russian Federation of Basic Research (project 15-03-06546).

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Authors and Affiliations

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

    Yurii V. Kharitonov, Makhmut M. Shakirov & Elvira E. Shults

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

    Yurii V. Kharitonov & Elvira E. Shults

Authors
  1. Yurii V. Kharitonov
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  2. Makhmut M. Shakirov
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  3. Elvira E. Shults
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Correspondence to Elvira E. Shults.

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10847_2016_596_MOESM1_ESM.docx

Supporting Information File 1: Experimental details and spectroscopic data of new compounds. Supplementary material 1 (DOCX 2768 kb)

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Kharitonov, Y.V., Shakirov, M.M. & Shults, E.E. Synthesis and spectroscopic studies of chiral macrocyclic furanolabdanoids connected on the 16,17-positions by 1,2,3-triazole rings with methylene or oxamethylene units. J Incl Phenom Macrocycl Chem 84, 197–202 (2016). https://doi.org/10.1007/s10847-016-0596-1

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