Amat Tusón, MercedesPérez Bosch, MariaLlor Brunés, NúriaEscolano Mirón, CarmenLuque Garriga, F. XavierMolins i Grau, EliesBosch Cartes, Joan2020-05-132020-05-132004-11-060022-3263https://hdl.handle.net/2445/159897The 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.13 p.application/pdfeng(c) American Chemical Society , 2004AlcaloidesLactamesSíntesi orgànicaAlkaloidsLactamsOrganic synthesisinfo:eu-repo/semantics/article5685092020-05-13info:eu-repo/semantics/openAccess