Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 7, Pages 2411-2414Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo1000274
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- Prof. Jean-Yves Lallemand (ICSN)
- University Montpellier 1 [BQR-2009]
- Centre National de la Recherche Scientifique
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The first total synthesis of 15-D-2t-isoprostane is described. (-)-(9S, 15S)-15-D-2t-IsoP 1 and (+)-(11R, 15R)-15-epi-15-E-2t-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of the cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules.
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