Szu-Han Chen
National Taiwan University, Taiwan
Posters & Accepted Abstracts: Med Chem (Los Angeles)
Dielsâ??Alder reactions are particularly useful for the total synthesis of pharmacologically active compounds and natural products. Not only does this strategy construct two new Câ??C Ï?-bonds in one step, but it also forms a cyclohexene system with good regioand stereo-selectivity up to four contiguous stereocenters. Using heteroatom-substituted electron-rich dienes, such as Danishefskyâ??s diene, usually promotes the normal electron-demand Dielsâ??Alder reactions in highly regioselective fashion. Tamiflu, the phosphate salt of oseltamivir, is a popular anti-influenza drug in clinical use. Dielsâ??Alder reactions using 1,3-butadiene, 1-timethylsilyoxy-1,3- butadiene, furan, N-Boc-pyrrole and 1-Cbz-1,2-dihydropyridine have been successfully applied to react with appropriate dienophiles for construction of the cyclohexene core structure of oseltamivir. We synthesized a novel diene precursor bearing both 3-pentoxy and ester groups. Dimerization of this diene was overcome by trapping it in situ using activated alkenes as the dienophiles. Inspired by Shibasakiâ??s work, we successfully synthesized a racemic mixture of oseltamivir via a sequence of reactions that comprise acyl azide formation and Curtius rearrangement. The synthesis of optically active oseltamivir via asymmetric Dielsâ??Alder reaction is currently under investigation.
Szu-Han Chen received her BS in Chemistry from Fu Jen Catholic University in 2008 and her MS degree in Chemistry from National Taiwan Normal University in 2010. She is a PhD student in the Department of Chemistry, National Taiwan University. Her research interests are in total synthesis of drug molecules as well as medicinal and biological chemistry.
Email: d99223108@ntu.edu.tw
Medicinal Chemistry received 6627 citations as per Google Scholar report
Spanish 
Chinese 
Russian 
German 
French 
Japanese 
Portuguese 
Hindi 