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

Verfasser / Beitragende:
[D. Shklyaruck]
Ort, Verlag, Jahr:
2015
Enthalten in:
Russian Journal of Organic Chemistry, 51/4(2015-04-01), 582-590
Format:
Artikel (online)
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024 7 0 |a 10.1134/S107042801504020X  |2 doi 
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100 1 |a Shklyaruck  |D D.  |u Belarusian State University, pr. Nezavisimosti 4, 220030, Minsk, Belarus  |4 aut 
245 1 0 |a New synthesis of syn -stereodiad building block for polyketides. Formal synthesis of arenamides A and C  |h [Elektronische Daten]  |c [D. Shklyaruck] 
520 3 |a 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). 
540 |a Pleiades Publishing, Ltd., 2015 
773 0 |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/4(2015-04-01), 582-590  |x 1070-4280  |q 51:4<582  |1 2015  |2 51  |o 11178 
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950 |B NATIONALLICENCE  |P 100  |E 1-  |a Shklyaruck  |D D.  |u Belarusian State University, pr. Nezavisimosti 4, 220030, Minsk, Belarus  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Russian Journal of Organic Chemistry  |d Pleiades Publishing  |g 51/4(2015-04-01), 582-590  |x 1070-4280  |q 51:4<582  |1 2015  |2 51  |o 11178