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DC Field | Value | Language |
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dc.contributor.author | Yayik, Nihan | - |
dc.contributor.author | Pérez Bosch, Maria | - |
dc.contributor.author | Molins i Grau, Elies | - |
dc.contributor.author | Bosch Cartes, Joan | - |
dc.contributor.author | Amat Tusón, Mercedes | - |
dc.date.accessioned | 2021-02-01T12:36:12Z | - |
dc.date.available | 2021-02-01T12:36:12Z | - |
dc.date.issued | 2021-01-15 | - |
dc.identifier.issn | 1420-3049 | - |
dc.identifier.uri | http://hdl.handle.net/2445/173571 | - |
dc.description.abstract | A synthetic route for the enantioselective construction of the tetracyclic spiro[indolizidine-1,3'-oxindole] framework present in a large number of oxindole alkaloids, with a cis H-3/H-15 stereochemistry, a functionalized two-carbon substituent at C-15, and an E-ethylidene substituent at C-20, is reported. The key steps of the synthesis are the generation of the tetracyclic spirooxindole ring system by stereoselective spirocyclization from a tryptophanol-derived oxazolopiperidone lactam, the removal of the hydroxymethyl group, and the stereoselective introduction of the E-ethylidene substituent by acetylation at the -position of the lactam carbonyl, followed by hydride reduction and elimination. Following this route, the 21-oxo derivative of the enantiomer of the alkaloid 7(S)-geissoschizol oxindole has been prepared. | - |
dc.format.extent | 15 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | MDPI | - |
dc.relation.isformatof | Reproducció del document publicat a: https://doi.org/10.3390/molecules26020428 | - |
dc.relation.ispartof | Molecules, 2021, vol. 26, p. 428-442 | - |
dc.relation.uri | https://doi.org/10.3390/molecules26020428 | - |
dc.rights | cc-by (c) Yayik, Nihan et al., 2021 | - |
dc.rights.uri | http://creativecommons.org/licenses/by/3.0/es | - |
dc.source | Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia) | - |
dc.subject.classification | Alcaloides | - |
dc.subject.classification | Enantiòmers | - |
dc.subject.classification | Compostos heterocíclics | - |
dc.subject.classification | Síntesi orgànica | - |
dc.subject.other | Alkaloids | - |
dc.subject.other | Enantiomers | - |
dc.subject.other | Heterocyclic compounds | - |
dc.subject.other | Organic synthesis | - |
dc.title | Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/publishedVersion | - |
dc.identifier.idgrec | 705965 | - |
dc.date.updated | 2021-02-01T12:36:12Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 33467493 | - |
Appears in Collections: | Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia) |
Files in This Item:
File | Description | Size | Format | |
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705965.pdf | 1.81 MB | Adobe PDF | View/Open |
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