Título:
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Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (−)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline
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Autor/a:
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Pinto, Alexandre; Piccichè, Miriam; Griera Farres, Rosa; Molins i Grau, Elies; Bosch Cartes, Joan; Amat Tusón, Mercedes
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Otros autores:
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Universitat de Barcelona |
Abstract:
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The synthesis of the Lycopodium alkaloids, (-)-cermizine B, (+)-serratezomine E, and (+)-luciduline using phenylglycinol-derived tricyclic lactams as chiral scaffolds, is reported. The requisite lactams are prepared by a cyclocondensation reaction between ( R)- or ( S)-phenylglycinol and the substituted δ-keto ester 11, easily accessible from ( R)-pulegone. The factors governing the stereoselectivity of these cyclocondensation reactions are discussed. Key steps of the synthesis from the stereochemical standpoint are the stereoselective elaboration of the allyl substituent to the ( S)-2-(piperidyl)methyl moiety and the stereoselective removal of the chiral inductor to give a cis-decahydroquinoline. |
Materia(s):
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-Alcaloides -Lactames -Catàlisi asimètrica -Síntesi asimètrica -Alkaloids -Lactams -Enantioselective catalysis -Asymmetric synthesis |
Derechos:
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(c) American Chemical Society , 2018
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Tipo de documento:
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Artículo Artículo - Versión aceptada |
Editor:
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American Chemical Society
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Compartir:
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