VESTNIK
Bashkirskogo universiteta

RUSSIAN
ISSN 1998-4812

Archive | Volume 18, 2013, No. 1.

OXIDATION OF RICINOLEIC ACID DERIVATIVES IN DIRECTED SYNTHESIS

Vestnik Bashkirskogo Universiteta. 2013. Vol. 18. No. 1. Pp. 27-35.
Ishmuratov G. Yu.
Institute of Organic Chemistry, Ufa Scientific Centre of the Russian Academy of Sciences
71 Prospekt Oktyabrya, 450054 Ufa, Republic of Bashkortostan, Russia.
Email: insect@anrb.ru
Yakovleva M. P.
Institute of Organic Chemistry, Ufa Scientific Centre of the Russian Academy of Sciences
71 Prospekt Oktyabrya, 450054 Ufa, Republic of Bashkortostan, Russia.
Vydrina V. A.
Institute of Organic Chemistry, Ufa Scientific Centre of the Russian Academy of Sciences
71 Prospekt Oktyabrya, 450054 Ufa, Republic of Bashkortostan, Russia.
Shayakhmetova A. Kh.
Institute of Organic Chemistry, Ufa Scientific Centre of the Russian Academy of Sciences
71 Prospekt Oktyabrya, 450054 Ufa, Republic of Bashkortostan, Russia.
Nazarov I. S.
Institute of Organic Chemistry, Ufa Scientific Centre of the Russian Academy of Sciences
71 Prospekt Oktyabrya, 450054 Ufa, Republic of Bashkortostan, Russia.
Kharisov R. Ya.
Institute of Organic Chemistry, Ufa Scientific Centre of the Russian Academy of Sciences
71 Prospekt Oktyabrya, 450054 Ufa, Republic of Bashkortostan, Russia.
Muslukhov R. R.
Institute of Organic Chemistry, Ufa Scientific Centre of the Russian Academy of Sciences
71 Prospekt Oktyabrya, 450054 Ufa, Republic of Bashkortostan, Russia.
Ishmuratova N. M.
Institute of Organic Chemistry, Ufa Scientific Centre of the Russian Academy of Sciences
71 Prospekt Oktyabrya, 450054 Ufa, Republic of Bashkortostan, Russia.

Abstract

The results of the authors’ investigations in expanding the synthetic potential of (R,Z)-(+)-12-hydroxy-9-octadecenoic (ricinoleic) acid via oxidative transformations (ozonolysis, functionalization of alkyl chemically stable alkyl (C-13÷C-18) part by the Barton reaction and hydroboration-oxidation of the double bond) in the directed synthesis are reviewed. The regioselectivity in the hydroboration-oxidation of methyl ester of the ricinoleic acid significantly depends on the configuration of the optically active center: the fraction of the resulting 1.3-diol is 74% larger than that of the 1.4-isomer. The new asymmetric center forms preferentially the (S)-configuration: 1.3-diol up to 87% and the 1.4-diol up to 100%.

Keywords

  • • ricinoleic acid
  • • castor oil
  • • ozonolysis
  • • Barton reaction
  • • hydroboration-oxidation

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