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Chemistry of Natural Compounds

, Volume 54, Issue 3, pp 478–480 | Cite as

Hydroboration by Diborane of Methyl Abietate

  • V. A. Vydrina
  • A. A. Kravchenko
  • M. P. Yakovleva
  • R. R. Muslukhov
  • A. G. Tolstikov
  • G. Yu. Ishmuratov
Article
  • 5 Downloads

Hydroboration-oxidation of methyl abietate by diborane in THF occurred preferentially at the sterically unhindered β-side of the molecule without involving the ester. The known hydroboration-oxidation product methyl 7β-hydroxy-13α-isopropylpodocarp-8(14)-en-15α-oate and previously unknown methyl 7β-hydroxy-13-isopropyl-8β-podocarp-13(14)-en-15α-oate, 14β-hydroxy-13α-isopropylpodocarp-7(8)-en-15α-oate, and 7β,14-dihydroxy-13α-isopropyl-8β-podocarpan-15α-oate, i.e., products from monohydroboration-oxidation at the ∆7,8- and ∆13,14-bonds without their respective shifts and from dihydroboration, were obtained.

Keywords

methyl abietate diborane-THF complex mono- and dihydroboration 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • V. A. Vydrina
    • 1
  • A. A. Kravchenko
    • 1
  • M. P. Yakovleva
    • 1
  • R. R. Muslukhov
    • 1
  • A. G. Tolstikov
    • 1
  • G. Yu. Ishmuratov
    • 1
  1. 1.Ufa Institute of ChemistryUfaRussia

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