Artículo
Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer–Villiger oxidation
Rudroff, Florian; Bianchi, Dario Alejandro
; Moran Ramallal, Roberto; Iqbal, Naseem; Dreier, Dominik; Mihovilovic, Marko D.
Fecha de publicación:
06/2016
Editorial:
Pergamon-Elsevier Science Ltd
Revista:
Tetrahedron
ISSN:
0040-4020
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
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.
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Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO
Articulos de INST.DE QUIMICA ROSARIO
Citación
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
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