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Synthetic Transformations of Higher Terpenoids. XXXIV.* Preparation of Carboxyl Derivatives of Isopimaric Acid

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Chemistry of Natural Compounds Aims and scope

New isopimaric acid derivatives containing amines and methyl esters of α-, β-, and ω-amino acids were prepared. Conditions were found for cyclic isomerisation of isopimaric acid propargylamide into 2-(dodecahydrophenanthren-1-yl)-5-methyloxazole or 2-(dodecahydrophenanthren-1-yl)-5-methylene-4,5-dihydrooxazole. The latter was selectively modified by adding the methyl ester of (2-methylamino)butanoic acid at the oxazole C-5 position.

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Acknowledgment

The work was supported financially by RFBR Grant No. 12-03-00535 and a grant of the RF President for Support of Leading Scientific Schools (No. NSh-2625.2014.3).

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Authors and Affiliations

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

    M. A. Timoshenko, A. B. Ayusheev, Yu. V. Kharitonov, M. M. Shakirov & E. E. Shul’ts

  2. Novosibirsk State University, 630090, Novosibirsk, Ul. Piragova, 2, Russia

    M. A. Timoshenko & A. B. Ayusheev

Authors
  1. M. A. Timoshenko
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  2. A. B. Ayusheev
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  3. Yu. V. Kharitonov
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  4. M. M. Shakirov
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  5. E. E. Shul’ts
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Corresponding author

Correspondence to E. E. Shul’ts.

Additional information

*For No. XXXIII, see [1].

Translated from Khimiya Prirodnykh Soedinenii, No. 4, July-August, 2014, pp. 583–589.

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Timoshenko, M.A., Ayusheev, A.B., Kharitonov, Y.V. et al. Synthetic Transformations of Higher Terpenoids. XXXIV.* Preparation of Carboxyl Derivatives of Isopimaric Acid. Chem Nat Compd 50, 673–680 (2014). https://doi.org/10.1007/s10600-014-1050-5

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  • DOI: https://doi.org/10.1007/s10600-014-1050-5

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