New Access to Kainic Acid via Intramolecular Palladium-Catalyzed Allylic Alkylation

New Access to Kainic Acid via Intramolecular Palladium-Catalyzed Allylic Alkylation

Abstract The formal synthesis of kainic acid was carried out in eleven steps. The key cyclization step was accomplished through an intramolecular palladium-catalyzed allylic alkylation of an allylic sulfone. Further functionalization of the resulting pyrrolidone ­featured, inter alia, a N-heterocycl...

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Veröffentlicht in:Synlett 2007-06, Vol.2007 (10), p.1521-1524
Hauptverfasser: Thuong, Mathieu Bui, Sottocornola, Silvia, Prestat, Guillaume, Broggini, Gianluigi, Madec, David, Poli, Giovanni
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Sprache:eng
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Zusammenfassung:Abstract The formal synthesis of kainic acid was carried out in eleven steps. The key cyclization step was accomplished through an intramolecular palladium-catalyzed allylic alkylation of an allylic sulfone. Further functionalization of the resulting pyrrolidone ­featured, inter alia, a N-heterocyclic carbene-copper hydride (NHC-CuH)-mediated stereoconvergent conjugate reduction.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2007-982542