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Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps
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SYSNO ASEP 0489527 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps Tvůrce(i) Jagtap, Pratap (UOCHB-X)
Císařová, I. (CZ)
Jahn, Ullrich (UOCHB-X) ORCIDZdroj.dok. Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520
Roč. 16, č. 5 (2018), s. 750-755Poč.str. 6 s. Jazyk dok. eng - angličtina Země vyd. GB - Velká Británie Klíč. slova isomerization ; radicals ; dimerization ; lignans ; electron transfer Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry CEP GA203/09/1936 GA ČR - Grantová agentura ČR Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000423787600011 EID SCOPUS 85041569994 DOI 10.1039/c7ob02848b Anotace A very short three-step approach to trans, trans, trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to a, beta-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2019 Elektronická adresa http://pubs.rsc.org/en/content/articlehtml/2018/ob/c7ob02848b
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