Počet záznamů: 1
Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl-alkyl coupling reactions as the key steps
- 1.
SYSNO ASEP 0482665 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl-alkyl coupling reactions as the key steps Tvůrce(i) Smrček, Jakub (UOCHB-X) ORCID
Pohl, Radek (UOCHB-X) RID, ORCID
Jahn, Ullrich (UOCHB-X) ORCIDZdroj.dok. Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520
Roč. 15, č. 44 (2017), s. 9408-9414Poč.str. 7 s. Jazyk dok. eng - angličtina Země vyd. GB - Velká Británie Klíč. slova in vivo ; eicosapentaenoic acid ; methyl ester Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000415342200017 EID SCOPUS 85034235067 DOI 10.1039/c7ob02505j Anotace A unified strategy for the total synthesis of the methyl esters of all phytoprostane (PhytoP) classes bearing two ring-oxygen atoms based on an orthogonally protected common precursor is described. Racemic 16-F-1t-, 16-E-1-PhytoP and their C-16 epimers, which also occur as racemates in Nature, were successfully obtained. The first total synthesis of very sensitive 16-D-1t-PhytoP succeeded, however, it quickly isomerized to more stable, but so far also unknown Delta(13)-16-D-1t-PhytoP, which may serve as a more reliable biomarker for D-type PhytoP. The dioxygenated cyclopentane ring carrying the omega-chain with the oxygen functionality in the 16-position was approached by a radical oxidative cyclization mediated by ferrocenium hexafluorophosphate and TEMPO. The alpha-chain was introduced by a new copper-catalyzed alkyl-alkyl coupling of a 6-heptenyl Grignard reagent with a functionalized cyclopentylmethyl triflate. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2018 Elektronická adresa http://pubs.rsc.org/en/content/articlehtml/2017/ob/c7ob02505j
Počet záznamů: 1