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Toward the Elucidation of the Metabolism of 15-E2-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite
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SYSNO ASEP 0345972 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Toward the Elucidation of the Metabolism of 15-E2-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite Author(s) Jahn, Ullrich (UOCHB-X) ORCID
Dinca, E. (DE)Number of authors 2 Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 75, č. 13 (2010), s. 4480-4491Number of pages 12 s. Language eng - English Country US - United States Keywords isoprostane ; total synthesis ; radical anion cyclization Subject RIV CC - Organic Chemistry CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000279030900016 DOI 10.1021/jo1006569 Annotation An 11-step total synthesis of the methyl ester of a potential metabolite of the autoxidatively formed natural product 15-E2-IsoP, whose metabolism is not known, is reported. Several vinylogous Mukaiyama aldol additions were tested for the assembly of the acyclic C7-C20 precursor. A new oxidative dianion cyclization served to access the cyclopentane core. The full carbon skeleton was synthesized by an acetylide alkylation. The overall yield of the metabolite amounts to 1.4% for the most efficient route. The results demonstrate convincingly that E2-IsoP metabolites are highly epimerization-sensitive and that they may thus also contribute to PGE2-action and metabolism. 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 2011
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