First total synthesis of vialinin A, a novel and extremely potent inhibitor of TNF-alpha production.
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.
Ye
Yue Qi
YQ
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan.
Koshino
Hiroyuki
H
Onose
Jun-ichi
J
Yoshikawa
Kunie
K
Abe
Naoki
N
Takahashi
Shunya
S
D001713:Biphenyl Compounds / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013730:Terphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors*
D001713:Biphenyl Compounds; D013730:Terphenyl Compounds; D014409:Tumor Necrosis Factor-alpha; C508745:vialinin A