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Studies On The Synthesis Of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis Of (-)-Cermizine B, (+)-Serratezomine E, And (+)-Luciduline.

A. Pinto, Miriam Piccichè, R. Griera, E. Molins, J. Bosch, M. Amat
Published 2018 · Chemistry, Medicine

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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.
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