Total synthesis and structural assignment of (−)-fusaequisin A

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dc.contributor.authorSchmidt, Ann-Christin
dc.contributor.authorHiersemann, Martin
dc.date.accessioned2022-03-04T13:49:13Z
dc.date.available2022-03-04T13:49:13Z
dc.date.issued2021-11-11
dc.description.abstract(−)-Fusaequisin A is an irregularly assembled polyketide isolated from the ascomycete Fusarium equiseti. Fusaequisin A shares a carbon backbone with curvicollide C from the ascomycete Podospora curvicolla but its absolute configuration remained hitherto unsettled. Herein, we document the total synthesis of (−)-fusaequisin A and its 4-O-desmethyl derivative following a central-to-lateral building block strategy. Catalytic asymmetric Claisen rearrangement, Julia-Kocienski olefination and olefin cross-metathesis served as key C/C-connecting transformations. The constitution and absolute configuration of (−)-fusaequisin A was deduced and the original structural assignment was adjusted.en
dc.identifier.urihttp://hdl.handle.net/2003/40764
dc.identifier.urihttp://dx.doi.org/10.17877/DE290R-22621
dc.language.isoende
dc.relation.ispartofseriesChemistry - a European journal;28(5)
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectAsymmetric synthesisen
dc.subjectNatural productsen
dc.subjectPolyketidesen
dc.subjectStructural elucidationen
dc.subjectTotal synthesisen
dc.subject.ddc540
dc.titleTotal synthesis and structural assignment of (−)-fusaequisin Aen
dc.typeTextde
dc.type.publicationtypearticlede
dcterms.accessRightsopen access
eldorado.secondarypublicationtruede
eldorado.secondarypublication.primarycitationA.-C. Schmidt, M. Hiersemann, Chem. Eur. J. 2022, 28, e202103558.de
eldorado.secondarypublication.primaryidentifierhttps://doi.org/10.1002/chem.202103558de

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