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http://hdl.handle.net/2445/128407
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DC Field | Value | Language |
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dc.contributor.author | Saborit Villarroya, Gisela | - |
dc.contributor.author | Bosch, Caroline | - |
dc.contributor.author | Parella, Teodor | - |
dc.contributor.author | Bradshaw, Ben | - |
dc.contributor.author | Bonjoch i Sesé, Josep | - |
dc.date.accessioned | 2019-02-19T10:08:14Z | - |
dc.date.available | 2019-02-19T10:08:14Z | - |
dc.date.issued | 2016-03-01 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/2445/128407 | - |
dc.description.abstract | A revised structure for the Lycopodium alkaloid huperzine N is proposed and confirmed by synthesis. The key synthetic steps involve an epimerization of a cis-5-oxodecahydroquinoline to the corresponding trans isomer and a coupling, followed by a diastereoselective hydrogenation using Wilkinson's catalyst to incorporate the pyridylmethyl moiety. This route allowed the alkaloid serralongamine A to be synthesized for the first time, and two additional steps led to the revised structure of huperzine N, both products bearing an unusual decahydroquinoline stereostructure. | - |
dc.format.extent | 6 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | American Chemical Society | - |
dc.relation.isformatof | Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.6b00025 | - |
dc.relation.ispartof | Journal of Organic Chemistry, 2016, vol. 81, num. 6, p. 2629-2634 | - |
dc.relation.uri | https://doi.org/10.1021/acs.joc.6b00025 | - |
dc.rights | (c) American Chemical Society , 2016 | - |
dc.source | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) | - |
dc.subject.classification | Alcaloides | - |
dc.subject.classification | Catàlisi | - |
dc.subject.classification | Síntesi orgànica | - |
dc.subject.classification | Ciclització (Química) | - |
dc.subject.classification | Productes naturals | - |
dc.subject.classification | Metodologia | - |
dc.subject.other | Alkaloids | - |
dc.subject.other | Catalysis | - |
dc.subject.other | Organic synthesis | - |
dc.subject.other | Ring formation (Chemistry) | - |
dc.subject.other | Natural products | - |
dc.subject.other | Methodology | - |
dc.title | Synthesis of (±)-Serralongamine A and the Revised Structure of Huperzine N | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 660714 | - |
dc.date.updated | 2019-02-19T10:08:14Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
dc.identifier.pmid | 26927208 | - |
Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) Articles publicats en revistes (Institut de Biomedicina (IBUB)) |
Files in This Item:
File | Description | Size | Format | |
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660714.pdf | 407.64 kB | Adobe PDF | View/Open |
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