Počet záznamů: 1

Toward the Elucidation of the Metabolism of 15-E2-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite

  1. 1.
    0345972 - UOCHB-X 2011 RIV US eng J - Článek v odborném periodiku
    Jahn, Ullrich - Dinca, E.
    Toward the Elucidation of the Metabolism of 15-E2-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite.
    Journal of Organic Chemistry. Roč. 75, č. 13 (2010), s. 4480-4491 ISSN 0022-3263
    Grant ostatní: DFG(DE) Ja896/3-1
    Výzkumný záměr: CEZ:AV0Z40550506
    Klíčová slova: isoprostane * total synthesis * radical anion cyclization
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 4.002, rok: 2010

    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.
    Trvalý link: http://hdl.handle.net/11104/0187123