Undergraduate researcher wins regional poster contest award

Anjola Uprety, an undergraduate who conducted research in Professor Wayland Noland’s laboratory last summer, won a Best Poster Award the Undergraduate Organic Poster session at a joint American Chemical Society Southeast Regional and Southwest Regional Meeting.

Her poster, "Diels-Alder Reactions of 2-Cycloalkenylthiophenes and Cycloalkenylbenzo[b]thiophenes," focused on newly synthesized compounds that will be offered to the National Institutes of Health to explore its anti-tumor, anti-bacterial, or other biological activities.

The heteroaromatic dienes 2-vinylthiophene 1 and 2-vinylbenzo[b]thiophene 2, with the vinyl groups fused to five-, six-, and seven-membered cycloalkene rings, underwent [4+2] cycloaddition reactions with substituted N-phenyl maleimides, gave isomerized endo-addition Diels-Alder adducts 6a-d (36-98%). Also isolated fully aromatized Diels-Alder adducts 4a-d (15-25%), and a highly diastereospecific (≥ 98% de) Michael-addition intermediates 5a-d (25-55%). This route to annulated thiophenes and benzo[b]thiophenes is versatile, and the starting materials are easily prepared.

The newly synthesized compounds will be offered to the National Institute of Health to explore its anti-tumor, anti-bacterial, or other biological activities.

Professor Noland is the principal investigator on this research, which also involved Honnaiah Vijay Kumar, Venkata Srinivasarao Narina, Uprety, Derek Aschbacher, Grant C. Flick, Hyejin Kim, and Jun Xie. Anjoli is an undergraduate at Wesleyan College in Macon GA.