PART 1: SYNTHESIS AND APPLICATION OF RECYCLABLE REAGENT AND CATALYST PART 2: SYNTHESIS OF A TRISACCHARIDE UNIT FROM K. PNEUMONIAE K-2044

Abstract

Part 1 consists of two projects which includes (i) the synthesis and application of a recyclable polymer-supported oxidant (Davis reagent) and (ii) the synthesis and application of a recyclable fluorous-tagged Pd catalyst.In the first project we have demonstrated that the oxidation of (i) alkenes, (ii) silyl enol ethers, (iii) pyridines and (iv) rearrangement of tetrahydrobenzimidazole could be achieved with the polymer-supported Davis reagent in high yields and short reaction time. In the second project, we have shown the use of fluorous-tagged oxime palladacycle as a catalyst in carbon-carbon cross-coupling reaction such as (i) Suzuki¿Miyaura reaction, (ii) Sonogashira reaction, (ii) Stille reaction, (iii) Heck reaction and (iv) Kumada reaction.Part 2 of the thesis focuses on the synthesis of a trisaccharide unit of a Capsular Polysaccharide (CPS) from K. pneumoniae NTUH-K2044. Hence, understanding the complete structure of CPS of PLA K. pneumoniae is important in determining clinical manifestations, and it was shown to consist of repeating units of the trisaccharide (->3)-ß-D-Glc-(1->4)-[2,3-(S)-pyruvate]-ß-D-GlcA-(1->3)-a-L-Fuc-(1-) and has the unusual feature of extensive pyruvation of glucuronic acid and acetylation at C3-OH of fucose.