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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 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps Author(s) Jagtap, Pratap (UOCHB-X)
Císařová, I. (CZ)
Jahn, Ullrich (UOCHB-X) ORCIDSource Title Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520
Roč. 16, č. 5 (2018), s. 750-755Number of pages 6 s. Language eng - English Country GB - United Kingdom Keywords isomerization ; radicals ; dimerization ; lignans ; electron transfer Subject RIV CC - Organic Chemistry OECD category Organic chemistry R&D Projects GA203/09/1936 GA ČR - Czech Science Foundation (CSF) Institutional support UOCHB-X - RVO:61388963 UT WOS 000423787600011 EID SCOPUS 85041569994 DOI 10.1039/c7ob02848b Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2019 Electronic address http://pubs.rsc.org/en/content/articlehtml/2018/ob/c7ob02848b
Number of the records: 1