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Total Synthesis of 15-F2t-Isoprostane by Using a New Oxidative Cyclization of Distonic Radical Anions as the Key Step
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SYSNO ASEP 0332943 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Total Synthesis of 15-F2t-Isoprostane by Using a New Oxidative Cyclization of Distonic Radical Anions as the Key Step Author(s) Jahn, Ullrich (UOCHB-X) ORCID
Dinca, E. (DE)Number of authors 2 Source Title Chemistry - A European Journal. - : Wiley - ISSN 0947-6539
Roč. 15, č. 1 (2009), s. 58-62Number of pages 5 s. Language eng - English Country DE - Germany Keywords cyclization ; electron transfer ; prostanoids ; radical ions Subject RIV CC - Organic Chemistry CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000262301900009 DOI 10.1002/chem.200802139 Annotation The shortest total synthesis of the major human cyclic lipid peroxidation metabolite, 15-F2t-IsoP in twelve steps and 14% overall yield is reported. Keysteps are a vinylogous aldol addition to construct the C7-C20 skeleton, an oxidative electron transfer-induced radical anion 5-exo cyclization to access the cyclopentane subunit and an acetylide alkylation to assemble the full skeleton of the natural product. 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 2010
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