The National Research Center for Carbohydrate Synthesis , Jiangxi Normal University , Nanchang , 330022 , China.
State Key Lab of Environmental Chemistry and Ecotoxicology , Research Center for Eco-environmental Science, CAS , Beijing , 100850 , China.
J Org Chem. 2018 Apr 6;83(7):4111-4118. doi: 10.1021/acs.joc.8b00008. Epub 2018 Mar 13.
The synthesis of both enantiomers of carambolaflavone A, the antidiabetic and flavonoid C-glycoside, was achieved for the first time via a 12-longest-linear-step with 16% (l-fucose) and 11% (d-fucose) overall yields. Through the synthetic investigation, the adverse effect of 4A MS in Suzuki C-glycosylation was disclosed, the mechanism of hydrogen-bonded-phenol involved Suzuki C-glycosylation was clarified, and the authentic structure of carambolaflavone A was also determined.
首次通过 12 步最长线性反应实现了具有抗糖尿病和类黄酮 C-糖苷结构的杨桃素 A 的对映异构体的全合成，总收率为 16%（L-岩藻糖）和 11%（D-岩藻糖）。通过合成研究，揭示了 4A MS 在铃木 C-糖苷化反应中产生的不利影响，阐明了涉及氢键酚的铃木 C-糖苷化反应的机理，并确定了杨桃素 A 的真实结构。
