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- W2014252302 abstract "An 11-step total synthesis of the methyl ester of a potential metabolite of the autoxidatively formed natural product 15-E(2)-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 E(2)-IsoP metabolites are highly epimerization-sensitive and that they may thus also contribute to PGE(2)-action and metabolism." @default.
- W2014252302 created "2016-06-24" @default.
- W2014252302 creator A5014563631 @default.
- W2014252302 creator A5043349363 @default.
- W2014252302 date "2010-06-09" @default.
- W2014252302 modified "2023-10-01" @default.
- W2014252302 title "Toward the Elucidation of the Metabolism of 15-E<sub>2</sub>-Isoprostane: The Total Synthesis of the Methyl Ester of a Potential Central Metabolite" @default.
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- W2014252302 doi "https://doi.org/10.1021/jo1006569" @default.
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