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Conjugate additions to phenylglycinol-derived unsaturated delta-lactams. Enantioselective synthesis of uleine alkaloids
Posted June 8th, 2010 by pschmidtke
| Title | Conjugate additions to phenylglycinol-derived unsaturated delta-lactams. Enantioselective synthesis of uleine alkaloids |
| Publication Type | Journal Article |
| Year of Publication | 2004 |
| Authors | Amat, M, Perez M, Llor N, Escolano C, Luque FJ, Molins E, Bosch J |
| Journal | The Journal of organic chemistry |
| Volume | 69 |
| Issue | 25 |
| Pagination | 8681 - 8693 |
| Date Published | 2004/12/10/ |
| Keywords | Alkaloids/chemical synthesis; Bridged Compounds/chemical synthesis; Crystallography, X-Ray; Glycine/analogs & derivatives/chemistry; Lactams/chemical synthesis; Molecular Conformation; Stereoisomerism |
| Abstract | 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. |
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