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http://hdl.handle.net/2445/159897| Title: | Conjugate Addition to Phenylglycinol-Derived Unsaturated ä-Lactams. Enantioselective Synthesos of Uleine Alkaloids |
| Author: | Amat Tusón, Mercedes Pérez Bosch, Maria Llor Brunés, Núria Escolano Mirón, Carmen Luque Garriga, F. Xavier Molins i Grau, Elies Bosch Cartes, Joan |
| Keywords: | Alcaloides Lactames Síntesi orgànica Alkaloids Lactams Organic synthesis |
| Issue Date: | 6-Nov-2004 |
| Publisher: | American Chemical Society |
| Abstract: | 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. |
| Note: | Versió postprint del document publicat a: https://doi.org/10.1021/jo0487101 |
| It is part of: | Journal of Organic Chemistry, 2004, vol. 69, num. 25, p. 8681-8693 |
| URI: | http://hdl.handle.net/2445/159897 |
| Related resource: | https://doi.org/10.1021/jo0487101 |
| ISSN: | 0022-3263 |
| Appears in Collections: | Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia) |
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|---|---|---|---|---|
| 568509.pdf | 286.04 kB | Adobe PDF | View/Open |
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