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Title: | Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (−)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline |
Author: | Pinto, Alexandre Piccichè, Miriam Griera Farres, Rosa Molins i Grau, Elies Bosch Cartes, Joan Amat Tusón, Mercedes |
Keywords: | Alcaloides Lactames Catàlisi asimètrica Síntesi asimètrica Alkaloids Lactams Enantioselective catalysis Asymmetric synthesis |
Issue Date: | 27-Jun-2018 |
Publisher: | American Chemical Society |
Abstract: | 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. |
Note: | Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.8b00983 |
It is part of: | Journal of Organic Chemistry, 2018, vol. 83, num. 15, p. 8364-8375 |
URI: | http://hdl.handle.net/2445/127620 |
Related resource: | https://doi.org/10.1021/acs.joc.8b00983 |
ISSN: | 0022-3263 |
Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) Articles publicats en revistes (Institut de Biomedicina (IBUB)) |
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