Expeditious synthesis of vialinin B, an extremely potent inhibitor of TNF-alpha production.
A first total synthesis of vialinin B, a powerful inhibitor (IC(50) 20 pM) of TNF-alpha production, is described. The key reactions include a double Suzuki-Miyaura coupling of electron-rich aryl bromide with a couple of phenylboronic acids, a Cu-mediated Ullmann reaction, and a LHMDS-promoted phenylacetylation. This synthesis proceeded in 11 steps with 18% overall yield from a known sesamol derivative.
Ye
Yue Qi
YQ
RIKEN, Wako, Saitama 351-0198, Japan.
Koshino
Hiroyuki
H
Onose
Jun-ichi
J
Yoshikawa
Kunie
K
Abe
Naoki
N
Takahashi
Shunya
S
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010648:Phenylacetates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors* / Q000096:biosynthesis
D001572:Benzofurans; D010648:Phenylacetates; D014409:Tumor Necrosis Factor-alpha; C515126:vialinin B