| 17850091 |
Ye YQ, Koshino H, Onose J, Yoshikawa K, Abe N, Takahashi S: First total synthesis of vialinin A, a novel and extremely potent inhibitor of TNF-alpha production. Org Lett. 2007 Oct 11;9(21):4131-4. Epub 2007 Sep 12.
Vialinin A, a powerful inhibitor (IC50 90 pM) of TNF-alpha production, was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid and an oxidative deprotection of bis-MOM ether. In addition, the related synthetic studies also suggest the necessity for structural revision of ganbajunin C, a positional isomer of vialinin A. |
2(0,0,0,2) |