Synthesis of chiral flavone-isochromane derivative

Abstract

I successfully synthesized the broom- and iodo-acetophenones (47a,b) in good yields, respectively. The benzylated dihydroxybenzaldehyde 48 was isolated in excellent yield. The Claisen-Schmidt condensation of compound 47a,b and 48 was successful with high yields for chalcone derivatives 49a,49b. The oxidative cyclisation of the chalcones 49a,b was carried out with catalytic amount of I2 with good yields for flavones 50a,b. The Suzuki coupling with the benzylated chiral boronic ester 51 was performed with the help of Pd(OAc)2 using Xantphos as ligand, and the isolation and identification of the new chiral alcohol 52 is in progress. After the successful purification, the formation of the isochromane derivative 53 can be performed.