Total Synthesis of (±)-Lysergic Acid, Lysergol, and Isolysergol by Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group

Ergot alkaloids and their synthetic analogs have been reported to exhibit broad biological activity. We investigated direct construction of the C/D ring system of ergot alkaloids based on palladium-catalyzed domino cyclization of amino allenes. With this biscyclization as the key step, total synthes...

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Veröffentlicht in:Organic letters 2008-11, Vol.10 (22), p.5239-5242
Hauptverfasser: Inuki, Shinsuke, Oishi, Shinya, Fujii, Nobutaka, Ohno, Hiroaki
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Sprache:eng
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Zusammenfassung:Ergot alkaloids and their synthetic analogs have been reported to exhibit broad biological activity. We investigated direct construction of the C/D ring system of ergot alkaloids based on palladium-catalyzed domino cyclization of amino allenes. With this biscyclization as the key step, total synthesis of (±)-lysergic acid, (±)-lysergol, and (±)-isolysergol was achieved.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8022648