dc.identifier.uri |
http://dx.doi.org/10.15488/104 |
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dc.identifier.uri |
http://www.repo.uni-hannover.de/handle/123456789/122 |
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dc.contributor.author |
Trost, B.M.
|
ger |
dc.contributor.author |
Osipov, M.
|
ger |
dc.contributor.author |
Krüger, Sebastian
|
ger |
dc.contributor.author |
Zhang, Y.
|
ger |
dc.date.accessioned |
2015-11-11T15:56:50Z |
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dc.date.available |
2015-11-11T15:56:50Z |
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dc.date.issued |
2014-07-30 |
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dc.identifier.citation |
Trost, B. M.; Osipov, M.; Krueger, S.; Zhang, Y.: A catalytic asymmetric total synthesis of (-)-perophoramidine. In: Chemical Science 6 (2015), Nr. 1, S. 349-353. DOI: http://dx.doi.org/10.1039/c4sc01826e |
ger |
dc.description.abstract |
We report a catalytic asymmetric total synthesis of the ascidian natural product perophoramidine. The synthesis employs a molybdenum-catalyzed asymmetric allylic alkylation of an oxindole nucleophile and a monosubstituted allylic electrophile as a key asymmetric step. The enantioenriched oxindole product from this transformation contains vicinal quaternary and tertiary stereocenters, and is obtained in high yield along with high levels of regio-, diastereo-, and enantioselectivity. To install the second quaternary stereocenter in the target, the route utilizes a novel regio- and diastereoselective allylation of a cyclic imino ether to deliver an allylated imino ether product in near quantitative yield and with complete regio- and diastereocontrol. Oxidative cleavage and reductive amination are used as final steps to access the natural product. |
eng |
dc.description.sponsorship |
John Stauffer Memorial Fellowship |
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dc.description.sponsorship |
Stanford Graduate Fellowship |
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dc.language.iso |
eng |
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dc.publisher |
Cambridge : Royal Society of Chemistry |
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dc.relation.ispartofseries |
Chemical Science 6 (2015), Nr. 1 |
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dc.rights |
CC BY-NC 3.0 Unported |
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dc.rights.uri |
http://creativecommons.org/licenses/by-nc/3.0/ |
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dc.subject |
enantioselective allylic alkylation |
eng |
dc.subject |
bond formation |
eng |
dc.subject |
(+)-perophoramidine |
eng |
dc.subject |
indoles |
eng |
dc.subject |
Pd |
eng |
dc.subject |
palladium |
eng |
dc.subject |
Perophora namei |
eng |
dc.subject |
enantioselektive allylische Alkylierung |
ger |
dc.subject |
Bindungsbildung |
ger |
dc.subject |
Synthese |
ger |
dc.subject |
(+)-Perophoramidin |
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dc.subject |
Perophoramidin |
ger |
dc.subject |
Perophora namei |
ger |
dc.subject |
Indol |
ger |
dc.subject |
Pd |
ger |
dc.subject |
Palladium |
ger |
dc.subject.classification |
Alkylierung |
ger |
dc.subject.classification |
Chemische Bindung |
ger |
dc.subject.classification |
Alkaloide |
ger |
dc.subject.classification |
Seescheiden |
ger |
dc.subject.classification |
Indol |
ger |
dc.subject.classification |
Palladium |
ger |
dc.subject.ddc |
540 | Chemie
|
ger |
dc.title |
A catalytic asymmetric total synthesis of (-)-perophoramidine |
eng |
dc.type |
Article |
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dc.type |
Text |
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dc.relation.essn |
2041-6539 |
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dc.relation.issn |
2041-6520 |
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dc.relation.doi |
http://dx.doi.org/10.1039/c4sc01826e |
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dc.bibliographicCitation.firstPage |
349 |
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dc.bibliographicCitation.lastPage |
353 |
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dc.description.version |
publishedVersion |
ger |
tib.accessRights |
frei zug�nglich |
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