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Synthetic Transformations of Higher Terpenoids. 36.* Synthesis of 13-(Oxazol-5-Yl)-15,16-Bisnorisopimaranes

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Chemistry of Natural Compounds Aims and scope

The conditions for oxidizing methyl isopimarate to the 15-oxo-15,16-dihydroisopimarate were studied. The latter was used for one-pot syntheses of 13-(oxazol-5-yl)-15,16-bisnorisopimarates that included formation of the 16-oxoaldehyde isopimarate and its condensation with α-amino acids. The structures of the synthesized compounds were confirmed by IR, UV, and NMR spectral data and an XSA.

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Acknowledgment

The work was financially supported by grants of the RFBR Nos. 15-03-06546 and 17-43-543235 (p_mol_a). Analytical and spectral studies were performed at the Chemical Service Center for Collective Use at NIOCh, SB, RAS. We thank E. G. Zhizhin and Yu. A. Rodikov for supplying the heteropolyacid-based oxidizing systems.

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 Prosp. Lavrent’eva, Novosibirsk, 630090, Russia

    M. A. Gromova, Yu. V. Kharitonov, T. V. Rybalova & E. E. Shul’ts

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

    T. V. Rybalova & E. E. Shul’ts

Authors
  1. M. A. Gromova
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  2. Yu. V. Kharitonov
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  3. T. V. Rybalova
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  4. E. E. Shul’ts
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Correspondence to E. E. Shul’ts.

Additional information

*For No. 35, see the literature [1].

Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2018, pp. 244–251.

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Gromova, M.A., Kharitonov, Y.V., Rybalova, T.V. et al. Synthetic Transformations of Higher Terpenoids. 36.* Synthesis of 13-(Oxazol-5-Yl)-15,16-Bisnorisopimaranes. Chem Nat Compd 54, 293–300 (2018). https://doi.org/10.1007/s10600-018-2327-x

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