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http://hdl.handle.net/2445/154828
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DC Field | Value | Language |
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dc.contributor.author | Bosch Hereu, Lluís | - |
dc.contributor.author | Mola Solà, Laura | - |
dc.contributor.author | Petit Roig, Elena | - |
dc.contributor.author | Saladrigas, Mar | - |
dc.contributor.author | Esteban Jarne, Jordi | - |
dc.contributor.author | Costa i Arnau, Anna M. | - |
dc.contributor.author | Vilarrasa i Llorens, Jaume | - |
dc.date.accessioned | 2020-04-02T09:43:13Z | - |
dc.date.available | 2020-04-02T09:43:13Z | - |
dc.date.issued | 2017-10-20 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/2445/154828 | - |
dc.description.abstract | A formal total synthesis of the cytotoxic macrolide amphidinolide E is reported. The strategic steps are three Julia-Kocienski reactions (J-K), for the formation of the C5-C6, C9-C10, and C17-C18 double bonds, a Suzuki-Molander C21-C22 bond formation reaction, and a Kita-Trost macrolactonization. The 'instability' of the two dienic systems and of the stereocenter at C2 (allylic methine, alpha to the carboxy group) and the protecting groups at C17-OH and C18-OH have posed difficult challenges. Each Julia-Kocienski olefination has been systematically optimized to provide the highest possible E/Z ratios. | - |
dc.format.extent | 14 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.7b01973 | - |
dc.relation.ispartof | Journal of Organic Chemistry, 2017, vol. 82, num. 20, p. 11021-11034 | - |
dc.relation.uri | https://doi.org/10.1021/acs.joc.7b01973 | - |
dc.rights | (c) American Chemical Society , 2017 | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Síntesi orgànica | - |
dc.subject.classification | Enllaços químics | - |
dc.subject.other | Organic synthesis | - |
dc.subject.other | Chemical bonds | - |
dc.title | Formal total synthesis of amphidinolide E | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 677636 | - |
dc.date.updated | 2020-04-02T09:43:13Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
Files in This Item:
File | Description | Size | Format | |
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677636.pdf | 988.75 kB | Adobe PDF | View/Open |
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