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Conjugate Addition to Phenylglycinol-Derived Unsaturated ä-Lactams. Enantioselective Synthesos of Uleine Alkaloids Amat Tusón, Mercedes Pérez Bosch, Maria Llor Brunés, Núria Escolano Mirón, Carmen Luque Garriga, F. Xavier Molins i Grau, Elies Bosch Cartes, Joan Alcaloides Lactames Síntesi orgànica Alkaloids Lactams Organic synthesis The stereochemical outcome of the conjugate addition of a variety of stabilized nucleophiles (2indoleaceticenolatesandsulfur-stabilizedanions)tothephenylglycinol-derivedunsaturatedlactams trans-2, cis-2, and its 8-ethyl-substituted analogue 10 is studied. The factors governing the exo or endo facial stereoselectivity are discussed. This methodology provides short synthetic routes to either cis- ortrans-3,4-disubstituted enantiopure piperidines as well as efficient routes for the enantioselective construction of the tetracyclic ring system of uleine alkaloids, both in the normal and 20-epi series. The formal total synthesis of several alkaloids of this group is reported. 2020-05-13T07:01:29Z 2020-05-13T07:01:29Z 2004-11-06 2020-05-13T07:01:29Z info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 0022-3263 https://hdl.handle.net/2445/159897 568509 eng Versió postprint del document publicat a: https://doi.org/10.1021/jo0487101 Journal of Organic Chemistry, 2004, vol. 69, num. 25, p. 8681-8693 https://doi.org/10.1021/jo0487101 (c) American Chemical Society , 2004 info:eu-repo/semantics/openAccess 13 p. application/pdf American Chemical Society Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)