Selective bromination of dihydroquinopimaric acid View Full Text


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Article Info

DATE

2011-09

AUTHORS

I. E. Smirnova, O. B. Kazakova, E. V. Tret’yakova, A. N. Lobov, L. V. Spirikhin, G. A. Tolstikov, K. Yu. Suponitskii

ABSTRACT

The reaction of dihydroquinopimaric acid methyl ester with bromine was found to be chemo- and stereoselective. Regardless of the solvent (acetic acid, methanol, dioxane), bromination of the title compound with an equimolar amount of bromine occurs as electrophilic addition at the double C19=C20 bond with formation of 14α-hydroxy- or 14α-methoxy-19R-bromo derivatives. The reaction with excess bromine (3 equiv) leads to the formation of 16S-bromo derivatives. The bromination process is accompanied by formation of epoxy bridge between the C14 and C20 atoms. X-Ray analysis revealed two polymorphic modifications of (16S,19R)-16,19-dibromo-14β,20-epoxydihydroquinopimaric acid methyl ester. More... »

PAGES

1385

References to SciGraph publications

  • 2010-08. Regioselective bromination of quinopimaric acid derivatives in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1134/s1070428011090223

    DOI

    http://dx.doi.org/10.1134/s1070428011090223

    DIMENSIONS

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