ol0c02335_si_002.pdf (4.9 MB)
Total Synthesis of Gastrodinol via Photocatalytic 6π Electrocyclization
journal contribution
posted on 2020-08-24, 14:36 authored by Yong-Feng Lv, Fu-Cai Ren, Meng-Ting Kuang, Yu Miao, Zhi-Lan Li, Jiang-Miao Hu, Jun ZhouThe first total synthesis
of gastrodinol, an unprecedented poly-p-cresol-substituted
natural product with a rearranged and reconstructed C ring moiety,
is reported. Our synthesis features a convergent fragment approach.
The Sonogashira coupling reaction forges the two segments together
to furnish the conjugated ene–yne. Photocatalytic 6π
electrocyclization followed by spontaneous aromatization is used to
construct the tetrasubstituted B ring at the late stage. Further study
shows that gastrodinol exhibits significant cytotoxic activity against
five human cancer cell lines in vitro (IC50 2.5–3.8 μM).