Identifier: TFG:1359
Authors: Lopez Balada, Anna
Abstract:
The research in new medication is both in the past and in the present an important research camp around the world due the huge number of new bacterial, and the bacterial which develops defences against the current medication. The aim of this project is to be able to synthesize the bhimamycin A, a natural antibiotic which can be isolated from the Streptomyces spin a laboratory, using the Ethyl-L-lactate as a reagent that is commercially available. The synthesis is composed by 3 parts, the first one, produced by Dr. Neumaier, is the synthesis of the 2-acetyl-8-methoxynaphthale-1,4-dione, which is a Michael acceptor, from O-methoxybenzoic acid. The second part is the synthesis of (R) -2- (benzyloxy) propanal from ethyl-L-lactate using oxidation and reduction reactions. Finally, the last part begins by adding the aldehyde to the Michael acceptor using the Corey-Seebach reaction or the Stetter reaction to make the 1,4- addition possible. Once this addition is made, a catalysis is necessary for the ciclation of the product, and a Lewis acid to deprotect the alcohol. To be able to do this work, most of the reaction has been done under inert atmosphere, purified with flash chromatogaphy and characteritzed with NMR, HPLC-MS and TLC-MS.
Repositori URV