Synthesis and Characterization of 6-Bromo-Benzoflavanone Derivatives

Abstract

This thesis presents the development of an efficient synthesis pathway for 6-bromo-benzoflavanone as aromatase inhibition for cancer treatment, aiming to optimize yield and enhance stereoselectivity. The process begins with the bromination of 1-(1-hydroxynaphthalen-2-yl)ethan-1-one, followed by protection of the hydroxyl group, and Claisen-Schmidt condensation to form chalcone derivatives with variable yields. Microwave-assisted cyclization using trifluoroacetic acid was employed after unsuccessful attempts with other cyclization methods, resulting in a 28% yield of the target flavanone compound. Then the 6-bromo-benzoflavanone is utilized as a reference compound in rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to chromenones, yielding high enantioselectivities, and its structure was confirmed through NMR.