Organic Seminar: Gong Chen, Nankai University
C-H Functionalization Strategy for Synthesis of Complex Peptides and Carbohydrates
a-Amino acids (aAA) are valuable chiral building blocks for synthesis. Despite significant advances in synthetic methodology, the efficient synthesis of enantiopure aAAs carrying complex side chains, as seen in numerous peptide natural products, remains challenging. A strategy based on the selective functionalization of side chain C−H bonds, particularly sp3 hybridized C−H bonds, of various readily available aAA precursors could provide a straightforward means for the synthesis and transformation of aAAs. In this talk, we will present our investigation of palladium-catalyzed auxiliary-directed C−H functionalization reactions for synthesis of aAAs and their application in the total synthesis of complex peptide natural products. Using the Pd-catalyzed intramolecular C(sp3)-H arylation reactions, we have also developed efficient and generally applicable strategies for constructing various peptide macrocycles bearing unique cyclophane brace. Lastly, we will present a simple bioinspired strategy for the stereoselective synthesis of C-aryl glycosides via Pd-catalyzed ortho-directed C(sp2)−H functionalization of arenes and heteroarenes with easily accessible glycosyl chloride donors.
Host: Maciej Walczak
Scheduling contact: Kayla Jones
Monday, February 3, 2020 at 4:00pm
Cristol Chemistry and Biochemistry, CHEM 142
1606 Central Campus Mall, Boulder, CO 80309