Title:First Synthesis of 2-Bromogentisyl Alcohol from Cultures of Penicillium
Concentricum
Volume: 20
Issue: 10
Author(s): Shaojun Shan*, Xiumei Lian, Jingxuan Li and Wensen Zhong
Affiliation:
- School of Pharmaceutical and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan,
528458, P.R. China
Keywords:
2-bromogentisyl alcohol, synthesis, penicillium, concentricum, cytotoxicity, breast cancer, 4-methoxyphenol.
Abstract: The first synthesis of 2-bromogentisyl alcohol, a halogenated compound cytotoxicity to
breast cancer cell line, was achieved in four steps. Key steps include (i) formylation of aromatic compound,
(ii) bromination, (iii) demethylation and (iv) reduction. Compound 3 was prepared from 4-
methoxyphenol (2) in 92% yield in the presence of MgCl2 and Et3N, then intermediate 4 was obtained
by bromination of 3 in 78% yield. Subsequently, the direct demethylation of 4 with BBr3 afforded the
intermediate 5 in 72% yield. Finally, title compound 1 was prepared by the reduction of 5 using
NaBH4 in 87% yield. The overall yield is 45% from 4-methoxyphenol. This method is simple and the
reaction conditions are mild.
