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http://hdl.handle.net/2445/135638
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DC Field | Value | Language |
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dc.contributor.author | Estarellas, Carolina | - |
dc.contributor.author | Arioli, Federica | - |
dc.contributor.author | Pérez Bosch, Maria | - |
dc.contributor.author | Are, Celeste | - |
dc.contributor.author | Hevia, David | - |
dc.contributor.author | Molins i Grau, Elies | - |
dc.contributor.author | Luque Garriga, F. Xavier | - |
dc.contributor.author | Bosch Cartes, Joan | - |
dc.contributor.author | Amat Tusón, Mercedes | - |
dc.date.accessioned | 2019-06-20T09:55:25Z | - |
dc.date.available | 2019-06-20T09:55:25Z | - |
dc.date.issued | 2017-07-25 | - |
dc.identifier.issn | 1434-193X | - |
dc.identifier.uri | http://hdl.handle.net/2445/135638 | - |
dc.description.abstract | Methyl-substituted Nazarov reagent 4 reacts stereoselectively with N-ind-Boc indoloquinolizidine lactams to give the expected 3-H/15-H cis pentacyclic yohimbine-type adducts when using 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) as the base. However, a dramatic change of the facial selectivity was observed when the reaction was performed in the presence of Cs2CO3, leading to the corresponding trans adducts. This annulation is the key step of a stereocontrolled synthesis of the 17acarba analogue of the heteroyohimbine alkaloid akuammigine. Theoretical calculations were used to rationalize the facial selectivity of these double Michael addition reactions. | - |
dc.format.extent | 11 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Wiley-VCH | - |
dc.relation.isformatof | Versió postprint del document publicat a: https://doi.org/10.1002/ejoc.201700610 | - |
dc.relation.ispartof | European Journal of Organic Chemistry, 2017, num. 27, p. 3969-3979 | - |
dc.relation.uri | https://doi.org/10.1002/ejoc.201700610 | - |
dc.rights | (c) Wiley-VCH, 2017 | - |
dc.source | Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia) | - |
dc.subject.classification | Teoria del funcional de densitat | - |
dc.subject.classification | Indicadors (Química) | - |
dc.subject.classification | Proves i reactius químics | - |
dc.subject.classification | Química orgànica | - |
dc.subject.other | Density functionals | - |
dc.subject.other | Indicators and test-papers | - |
dc.subject.other | Chemical tests and reagents | - |
dc.subject.other | Organic chemistry | - |
dc.title | Origin of the Base-Dependent Facial Selectivity in Annulation Reactions of Nazarov-Type Reagents with Unsaturated Indolo[2,3-a] quinolizidine Lactams | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 677698 | - |
dc.date.updated | 2019-06-20T09:55:25Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia) |
Files in This Item:
File | Description | Size | Format | |
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677698.pdf | 13.69 MB | Adobe PDF | View/Open |
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