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Please use this identifier to cite or link to this item: http://hdl.handle.net/1807/32228

Title: Oxidative Palladium(II)-catalyzed Arene C-H Bond Functionalization and Progress towards the Total Synthesis of 6-Deoxyerythronolide B
Authors: Borduas, Nadine
Advisor: Dong, Vy Maria
Department: Chemistry
Keywords: oxidative cross coupling
total synthesis
Issue Date: 21-Mar-2012
Abstract: To address the issue of unnecessary functional group transformations in synthesis, the direct functionalization of carbon-hydrogen (C―H) bonds presents itself as an efficient and atom economical process. In particular, palladium(II)-catalyzed oxidative functionalization of arene C–H bonds were investigated to yield intermolecular and intramolecular arylations. Kinetic studies and characterization of bimetallic palladium(II) complexes led to the discovery of two other palladium(II)-catalyzed processes: arene hydroxylation and selective chlorination of anilides. Realizing the potential of biocatalysis and of transition-metal catalysis, we marriaged these two fundamentally different methods to access complex molecules in rapid and step economical ways and chose popular synthetic target, 6-deoxyerythronolide B to showcase the efficiency of these stereoselective reactions. To form the 14-membered lactone, we employed a transition-metal catalyzed ring-closing metathesis. Two different fragments were assembled via traditional and reliable aldols, oxidations and reductions, crotylations and protective group chemistry.
URI: http://hdl.handle.net/1807/32228
Appears in Collections:Master

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