Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (−)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline

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 substit...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-06
Main Authors: Pinto, Alexandre, Piccichè, Miriam, Griera Farres, Rosa, Molins i Grau, Elies, Bosch Cartes, Joan, Amat Tusón, Mercedes
Format: Article
Language:English
Subjects:
Alcaloides
Alkaloids
Asymmetric synthesis
Catàlisi asimètrica
Enantioselective catalysis
Lactames
Lactams
Síntesi asimètrica
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Summary: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.
ISSN:0022-3263