A catalytic asymmetric total synthesis of (-)-perophoramidine

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dc.identifier.uri http://dx.doi.org/10.15488/104
dc.identifier.uri http://www.repo.uni-hannover.de/handle/123456789/122
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
dc.date.available 2015-11-11T15:56:50Z
dc.date.issued 2014-07-30
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. ger
dc.description.sponsorship John Stauffer Memorial Fellowship
dc.description.sponsorship Stanford Graduate Fellowship
dc.language.iso eng ger
dc.publisher Cambridge : Royal Society of Chemistry
dc.relation.ispartofseries Chemical Science 6 (2015), Nr. 1 ger
dc.rights CC BY-NC 3.0 ger
dc.rights.uri http://creativecommons.org/licenses/by-nc/3.0/ ger
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 ger
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
dc.type Text
dc.relation.essn 2041-6539
dc.relation.issn 2041-6520
dc.relation.doi http://dx.doi.org/10.1039/c4sc01826e
dc.description.version publishedVersion ger
tib.accessRights frei zug�nglich


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