Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 44, Pages 9408-9414Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob02505j
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- Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences [RVO:61388963]
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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.
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