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Zeitschriftenartikel:

F. Rudroff, D. Bianchi, R. Moran-Ramallal, N. Iqbal, D. Dreier, M.D. Mihovilovic:
"Synthesis of tetrahydrofuran-based natural products and their carba analogs via stereoselective enzyme mediated Baeyer-Villiger oxidation";
Tetrahedron, 72 (2016), S. 7212 - 7221.



Kurzfassung englisch:
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.

Schlagworte:
Showdomycin; Goniofufurone; Biotransformation; Asymmetric synthesis; Chemo-enzymatic; C-nucleosides; Carba-C-nucleosides


"Offizielle" elektronische Version der Publikation (entsprechend ihrem Digital Object Identifier - DOI)
http://dx.doi.org/10.1016/j.tet.2015.11.048


Erstellt aus der Publikationsdatenbank der Technischen Universität Wien.