Modified Total Synthesis of Verbenachalcone

作者:Zhang Ying-Peng*; Chen Yu-Tao; Yang Yun-Shang; Guan Xiao
来源:Chemical Journal of Chinese Universities, 2010, 31(7): 1342-1345.

摘要

A new and simple method for synthesis of verbenachalcone (1) was reported. A method for reverse synthesis design was adopted to two synthetic fragments, compound 4 and compound 6. Then the two fragments were combined together, starting from p-hydroxybenzaldehyde(2) through acetylation, bromination, Ullmann reaction, methoxymethylation, aldol condensation, deprotection, catalytic hydrogenation seven steps to target compound, with total yield of 39.1%. The key steps were the Ullmann reaction of 3-bromo-4-hydroxybenzaldehyde (3) with vanilline. The chemical structures of the key intermediate and final target product were verified by (1)H NMR, (13)C NMR and ESI-MS.