Publications in Scientific Journals:

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), 7212 - 7221.

English 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.

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

"Official" electronic version of the publication (accessed through its Digital Object Identifier - DOI)

Created from the Publication Database of the Vienna University of Technology.