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dc.contributor.author
Altmann, Karl-Heinz
dc.contributor.author
Bold, Christian P.
dc.contributor.author
Gut, Melanie
dc.contributor.author
Schürmann, Jasmine
dc.contributor.author
Lucena-Agell, Daniel
dc.contributor.author
Díaz, José F.
dc.contributor.author
Gertsch, Juerg
dc.date.accessioned
2021-04-08T12:14:40Z
dc.date.available
2021-01-29T18:22:28Z
dc.date.available
2021-02-26T15:50:57Z
dc.date.available
2021-04-08T12:14:40Z
dc.date.issued
2021-04-01
dc.identifier.issn
0947-6539
dc.identifier.issn
1521-3765
dc.identifier.other
10.1002/chem.202003996
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/466829
dc.description.abstract
We describe the convergent synthesis of three prototypical examples of a new class of analogues of the complex, cytotoxic marine macrolide (−)‐zampanolide that incorporate an embedded N‐substituted morpholine moiety in place of the natural tetrahydropyran ring. The final construction of the macrolactone core was based on a high‐yielding intramolecular HWE olefination, while the hemiaminal‐linked side chain was elaborated through a stereoselective, BINAL‐H‐mediated addition of (Z,E)‐sorbamide to a macrocyclic aldehyde precursor. The synthesis of the common functionalized morpholine building block involved two consecutive epoxide openings with tosylamide and the product of the first opening reaction, respectively, as nucleophiles. Of the three morpholino‐zampanolides investigated, the N‐acetyl and the N‐benzoyl derivatives both exhibited nanomolar antiproliferative activity, thus being essentially equipotent with the natural product. In contrast, the activity of the N‐tosyl derivative was significantly reduced. © 2020 Wiley‐VCH GmbH
en_US
dc.language.iso
en
en_US
dc.publisher
Wiley
en_US
dc.subject
Macrocyclization
en_US
dc.subject
Stereoselective aza aldol reaction
en_US
dc.subject
Structure–activity relationships
en_US
dc.subject
Total synthesis
en_US
dc.subject
Zampanolide
en_US
dc.title
Synthesis of Morpholine‐Based Analogs of (−)‐Zampanolide and Their Biological Activity
en_US
dc.type
Journal Article
dc.date.published
2020-10-20
ethz.journal.title
Chemistry - A European Journal
ethz.journal.volume
27
en_US
ethz.journal.issue
19
en_US
ethz.journal.abbreviated
Chem. Eur. J.
ethz.pages.start
5936
en_US
ethz.pages.end
5943
en_US
ethz.grant
Natural Products as Lead Structures for Anticancer and Antibacterial Drug Discovery: SAR Evaluation of Zampanolide and Pyridomycin
en_US
ethz.grant
Natural Products as Lead Structures for Anticancer and Antibacterial Drug Discovery: SAR Evaluation of Zampanolide and Pyridomycin
en_US
ethz.identifier.wos
ethz.identifier.scopus
ethz.publication.place
Weinheim
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)
en_US
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)
en_US
ethz.grant.agreementno
175744
ethz.grant.agreementno
149253
ethz.grant.fundername
SNF
ethz.grant.fundername
SNF
ethz.grant.funderDoi
10.13039/501100001711
ethz.grant.funderDoi
10.13039/501100001711
ethz.grant.program
Projektförderung in Mathematik, Natur- und Ingenieurwissenschaften (Abteilung II)
ethz.grant.program
Projekte MINT
ethz.date.deposited
2021-01-29T18:22:36Z
ethz.source
FORM
ethz.eth
yes
en_US
ethz.availability
Metadata only
en_US
ethz.rosetta.installDate
2021-04-08T12:14:50Z
ethz.rosetta.lastUpdated
2023-02-06T21:40:20Z
ethz.rosetta.versionExported
true
ethz.COinS
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