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Synthesis of epothilones molecule fragment (15R)-C13-C21 from D-mannitol

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Abstract

Efficient synthesis of an epothilone molecules fragment (15R)-C13-C21 was carried out from D-mannitol through its conversion into methyl 2,3-O-cyclohexylidene-D-glycerate followed by the cyclopropanation of the ester group with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide and the transformation of the obtained cyclopropanol into the corresponding 2-substituted allyl bromide. The coupling of the latter catalyzed by copper with 2-methylthiazolyl-4-magnesium bromide, the shift of a double carbon-carbon bond in the product obtained into the position, conjugated with the thiazole ring, and the common transformation of the protected 1,2-diol function afforded the target compound in 15% yield.

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Authors and Affiliations

  1. Belorussian State University, Minsk, 220030, Belarus

    V. N. Kovalenko, N. A. Sokolov & O. G. Kulinkovich

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  1. V. N. Kovalenko
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  2. N. A. Sokolov
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  3. O. G. Kulinkovich
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Correspondence to O. G. Kulinkovich.

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Original Russian Text © V.N. Kovalenko, N.A. Sokolov, O. G. Kulinkovich, 2010, published in Zhurnal Organicheskoi Khimii, 2010, vol. 46, No. 11, pp. 1694–1700.

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Kovalenko, V.N., Sokolov, N.A. & Kulinkovich, O.G. Synthesis of epothilones molecule fragment (15R)-C13-C21 from D-mannitol. Russ J Org Chem 46, 1702–1708 (2010). https://doi.org/10.1134/S1070428010110175

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  • DOI: https://doi.org/10.1134/S1070428010110175

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