Studies on natural p-terphenyls: total syntheses of vialinin A and terrestrin B.
A powerful inhibitor of TNF-alpha production, vialinin A, was synthesized from sesamol through a series of reactions involving double Suzuki-Miyaura coupling, 2,3-dichloro-5,6-dicyano-1,4-benzoquino (DDQ) mediated de-methoxymethylation and oxidative removal of methylene acetal by lead tetraacetate. The synthetic method also made it possible to prepare a related compound, terrestrin B.
Ye
Yue Qi
YQ
RIKEN, Wako, Saitama, Japan.
Koshino
Hiroyuki
H
Onose
Jun-ichi
J
Yoshikawa
Kunie
K
Abe
Naoki
N
Takahashi
Shunya
S
D016227:Benzoquinones / Q000737:chemistry; D002087:Butyrates / Q000138:chemical synthesis* / Q000737:chemistry; D013730:Terphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D016227:Benzoquinones; D002087:Butyrates; D013730:Terphenyl Compounds; C548352:terrestrin B; C508745:vialinin A; C000928:dichlorodicyanobenzoquinone