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New synthesis of syn-stereodiad building block for polyketides. Formal synthesis of arenamides A and C

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Abstract

An efficient procedure has been developed for the transformation of (7S)-7-(3-bromoprop-1-en-2-yl)-5,5-dimethyl-4,6-dioxaspiro[2.5]octane [available from diethyl (S)-malate] into methyl 2-[(4S)-2,2-dimethyl-5-methylidene-1,3-dioxan-4-yl]acetate, and conditions for diastereoselective reduction of the double C=C bond in the latter have been optimized. The reduction product has been converted into (3S,4S)-3-[tert-butyl(dimethyl)siloxy]-4-methyldecanoic acid which is a building block for the synthesis of arenamides A and C, natural compounds possessing pronounced antitumor activity and efficiently inhibiting nitrogen(II) oxide and prostaglandin E2 (PGE2).

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  1. Belarusian State University, pr. Nezavisimosti 4, Minsk, 220030, Belarus

    D. G. Shklyaruck

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  1. D. G. Shklyaruck
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Correspondence to D. G. Shklyaruck.

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Original Russian Text © D.G. Shklyaruck, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 4, pp. 599–606.

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Shklyaruck, D.G. New synthesis of syn-stereodiad building block for polyketides. Formal synthesis of arenamides A and C. Russ J Org Chem 51, 582–590 (2015). https://doi.org/10.1134/S107042801504020X

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