Total Synthesis of a Docosahexaenoic Acid Prostanoid Using an Intramolecular Organocatalytic Michael Reaction of a Formyl-Enal Derivative

Total Synthesis of a Docosahexaenoic Acid Prostanoid Using an Intramolecular Organocatalytic Michael Reaction of a Formyl-Enal Derivative

The total synthesis of a docosahexaenoic-acid-derived prostaglandin, 4,11-diepi-4-F4t-neuroprostane, featuring a complex lateral chain was achieved for the first time. A novel prostaglandin cyclopentane skeleton obtained via an intramolecular highly selective organocatalytic Michael sequence of a fo...

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Veröffentlicht in:Organic letters 2020-10, Vol.22 (19), p.7455-7459
Hauptverfasser: Revol-Cavalier, Johanna, Bultel-Poncé, Valérie, Guy, Alexandre, Durand, Thierry, Oger, Camille, Galano, Jean-Marie
Format: Artikel
Sprache:eng
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Chemical Sciences
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Zusammenfassung:The total synthesis of a docosahexaenoic-acid-derived prostaglandin, 4,11-diepi-4-F4t-neuroprostane, featuring a complex lateral chain was achieved for the first time. A novel prostaglandin cyclopentane skeleton obtained via an intramolecular highly selective organocatalytic Michael sequence of a formyl-enal derivative allowed the desired and exclusive thermodynamic trans configuration of the lipidic lateral chains.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02553