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dc.contributor.author
Rudroff, Florian
dc.contributor.author
Bianchi, Dario Alejandro
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dc.contributor.author
Moran Ramallal, Roberto
dc.contributor.author
Iqbal, Naseem
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Dreier, Dominik
dc.contributor.author
Mihovilovic, Marko D.
dc.date.available
2018-07-19T17:35:15Z
dc.date.issued
2016-06
dc.identifier.citation
Rudroff, Florian; Bianchi, Dario Alejandro; Moran Ramallal, Roberto; Iqbal, Naseem; Dreier, Dominik; et al.; Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer–Villiger oxidation; Pergamon-Elsevier Science Ltd; Tetrahedron; 72; 46; 6-2016; 7212-7221
dc.identifier.issn
0040-4020
dc.identifier.uri
http://hdl.handle.net/11336/52649
dc.description.abstract
In this work we present efficient formal syntheses of several biologically interesting natural products (showdomycin, goniofufurone, trans-kumausyne) and their novel carba analogs by applying different Baeyer–Villiger monooxygenases. This strategy provides access to tetrahydrofuran-based natural products, C-nucleosides and both antipodes of the corresponding carba analogs in high optical purities (up to >95% ee) starting from simple achiral and commercially available building blocks (tetrabromoacetone, furan and cyclopentadiene). The striking key features of this chemo-enzymatic approach are the introduction of four stereogenic centers in as few as three reaction steps within a desymmetrization approach and the short-cut of several reaction sequences by the implementation of a biocatalytic step.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Pergamon-Elsevier Science Ltd
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Asymmetric Synthesis
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Biotransformation
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C-Nucleosides
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Carba-C-Nucleosides
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Chemo-Enzymatic
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Goniofufurone
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Showdomycin
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Otras Ciencias Químicas
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer–Villiger oxidation
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-07-18T20:41:51Z
dc.journal.volume
72
dc.journal.number
46
dc.journal.pagination
7212-7221
dc.journal.pais
Reino Unido
dc.journal.ciudad
Oxford
dc.description.fil
Fil: Rudroff, Florian. Vienna University of Technology; Austria
dc.description.fil
Fil: Bianchi, Dario Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Vienna University of Technology; Austria
dc.description.fil
Fil: Moran Ramallal, Roberto. Vienna University of Technology; Austria
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Fil: Iqbal, Naseem. Vienna University of Technology; Austria. USAID Grantee; Pakistán
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Fil: Dreier, Dominik. Vienna University of Technology; Austria
dc.description.fil
Fil: Mihovilovic, Marko D.. Vienna University of Technology; Austria
dc.journal.title
Tetrahedron
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.1016/j.tet.2015.11.048
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040402015302325
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