Desymmetrization of C -Symmetric Bis(Boronic Esters) by Zweifel Olefinations.
dc.contributor.author | Linne, Yannick | |
dc.contributor.author | Schönwald, Axel | |
dc.contributor.author | Weißbach, Sebastian | |
dc.contributor.author | Kalesse, Markus | |
dc.date.accessioned | 2020-10-01T14:17:55Z | |
dc.date.available | 2020-10-01T14:17:55Z | |
dc.date.issued | 2020-06-03 | |
dc.identifier.citation | Chemistry. 2020 Jun 26;26(36):7998-8002. doi: 10.1002/chem.202000599. | en_US |
dc.identifier.pmid | 32068298 | |
dc.identifier.doi | 10.1002/chem.202000599 | |
dc.identifier.uri | http://hdl.handle.net/10033/622494 | |
dc.description.abstract | anti-Configured 1,3-dimethyl deoxypropionate motifs are important sub structures in natural products. Herein, we describe a bidirectional approach for the rapid construction of natural products featuring such motifs by using C2 -symmetrical 1,3-bis(boronic esters). As for its application in convergent syntheses it was important to establish a selective mono-Zweifel olefination we describe the scope and limitations by using different 1,3-bis(boronic esters) and nucleophiles. This protocol takes advantage of the combination of the Hoppe-Matteson-Zweifel chemistry, which was elegantly put into practice by Aggarwal et al. In order to show its applicability the total syntheses of two natural products, serricornin and (+)-invictolide, were performed. | en_US |
dc.language.iso | en | en_US |
dc.publisher | Wiley | en_US |
dc.rights | Attribution-NonCommercial-ShareAlike 4.0 International | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-sa/4.0/ | * |
dc.subject | C2-symmetry | en_US |
dc.subject | desymmetrization | en_US |
dc.subject | lithiation-borylation chemistry | en_US |
dc.subject | mono-Zweifel olefination | en_US |
dc.subject | natural product synthesis | en_US |
dc.title | Desymmetrization of C -Symmetric Bis(Boronic Esters) by Zweifel Olefinations. | en_US |
dc.type | Article | en_US |
dc.identifier.eissn | 1521-3765 | |
dc.contributor.department | HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany. | en_US |
dc.identifier.journal | Chemistry (Weinheim an der Bergstrasse, Germany) | en_US |
dc.source.volume | 26 | |
dc.source.issue | 36 | |
dc.source.beginpage | 7998 | |
dc.source.endpage | 8002 | |
refterms.dateFOA | 2020-10-01T14:17:56Z | |
dc.source.journaltitle | Chemistry (Weinheim an der Bergstrasse, Germany) | |
dc.source.country | Germany |