%0 Journal Article %J The Journal of organic chemistry %D 2004 %T Conjugate additions to phenylglycinol-derived unsaturated delta-lactams. Enantioselective synthesis of uleine alkaloids %A Amat,M. %A Perez,M. %A Llor,N. %A Escolano,C. %A F. J. Luque %A Molins,E. %A Bosch,J. %K Alkaloids/chemical synthesis; Bridged Compounds/chemical synthesis; Crystallography %K X-Ray; Glycine/analogs & derivatives/chemistry; Lactams/chemical synthesis; Molecular Conformation; Stereoisomerism %N 25 %P 8681 - 8693 %V 69 %X The stereochemical outcome of the conjugate addition of a variety of stabilized nucleophiles (2-indoleacetic enolates and sulfur-stabilized anions) to the phenylglycinol-derived unsaturated lactams 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- or trans-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. %8 2004/12/10/