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Synthesis and some transformations of (−)-carveol

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Abstract

Reduction of the oxo group in (−)-carvone with LiAlH4, NaBH4, and (i-Bu)2AlH was performed. It was found that the reduction with the system CeCl3 · 7 H2O-NaBH4 in methanol at 20°C is the most practical procedure for the synthesis of (−)-carveol. Solvolysis of (−)-carvyl methanesulfonate gave products of SN2 and SN2′ replacement of the methylsulfonyloxy group, the latter slightly prevailing. Overman rearrangement of (−)-carveol resulted in the formation of the corresponding trichloroacetamide derivative, and intramolecular iodoetherification of the title compound afforded 6-iodomethyl-2,6-dimethyl-7-oxabicyclo[3.2.1]oct-2-ene.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    R. F. Valeev, N. S. Vostrikov & M. S. Miftakhov

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  1. R. F. Valeev
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  2. N. S. Vostrikov
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  3. M. S. Miftakhov
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Correspondence to R. F. Valeev.

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Original Russian Text © R.F. Valeev, N.S. Vostrikov, M.S. Miftakhov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 6, pp. 828–831.

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Valeev, R.F., Vostrikov, N.S. & Miftakhov, M.S. Synthesis and some transformations of (−)-carveol. Russ J Org Chem 45, 810–814 (2009). https://doi.org/10.1134/S1070428009060025

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  • DOI: https://doi.org/10.1134/S1070428009060025

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