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dc.contributor.author
Brütsch, Tobias M.
dc.contributor.author
Berardozzi, Simone
dc.contributor.author
Rothe, Marlene L.
dc.contributor.author
Redondo-Horcajo, Mariano
dc.contributor.author
Díaz, José F.
dc.contributor.author
Altmann, Karl-Heinz
dc.date.accessioned
2020-12-21T09:19:47Z
dc.date.available
2020-12-20T03:40:23Z
dc.date.available
2020-12-21T09:19:47Z
dc.date.issued
2020-11-06
dc.identifier.issn
1523-7060
dc.identifier.issn
1523-7052
dc.identifier.other
10.1021/acs.orglett.0c02974
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/457334
dc.description.abstract
We have developed a new method for the stereoselective establishment of the N-acyl hemiaminal moiety in zampanolide-type structures that involves the reaction of (Z,E)-sorbamide (3) with BINAL-H and subsequent amide transfer from a putative aluminum carboximidoate complex to the aldehyde moiety of a dactylolide precursor, such as 2 or 5. The method has enabled the efficient synthesis of 13-desmethylene-(−)-zampanolide (4), which was found to be an equipotent cell growth inhibitor as the natural product (−)-zampanolide (1). © 2020 American Chemical Society
en_US
dc.language.iso
en
en_US
dc.publisher
American Chemical Society
en_US
dc.title
A Method for the Stereoselective Construction of the Hemiaminal Center in Zampanolides
en_US
dc.type
Journal Article
dc.date.published
2020-10-12
ethz.journal.title
Organic Letters
ethz.journal.volume
22
en_US
ethz.journal.issue
21
en_US
ethz.journal.abbreviated
Org. Lett.
ethz.pages.start
8345
en_US
ethz.pages.end
8348
en_US
ethz.identifier.wos
ethz.identifier.scopus
ethz.publication.place
Washington, DC
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02534 - Institut für Pharmazeutische Wiss. / Institute of Pharmaceutical Sciences::03647 - Altmann, Karl-Heinz (emeritus) / Altmann, Karl-Heinz (emeritus)
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02534 - Institut für Pharmazeutische Wiss. / Institute of Pharmaceutical Sciences::03647 - Altmann, Karl-Heinz (emeritus) / Altmann, Karl-Heinz (emeritus)
ethz.date.deposited
2020-12-20T03:40:27Z
ethz.source
SCOPUS
ethz.eth
yes
en_US
ethz.availability
Metadata only
en_US
ethz.rosetta.installDate
2020-12-21T09:19:57Z
ethz.rosetta.lastUpdated
2021-02-15T22:45:18Z
ethz.rosetta.exportRequired
true
ethz.rosetta.versionExported
true
ethz.COinS
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