Total Synthesis of Terprenin, a Novel Immunosuppressive p-Terphenyl Derivative.
We achieved a total synthesis of terprenin, a novel potent immunoglobulin E antibody suppressant which was obtained from the fermentation broth of Aspergillus candidus RF-5672 and has a highly oxygenated p-terphenyl skeleton with a prenyloxy side chain. The key steps relied on the Suzuki reaction to construct the terphenyl skeleton and on regioselective halogenations to selectively combine the aromatic rings. The highly efficient and practical production of this important natural product offers promise for the development of a new type of antiallergic drug.
Yonezawa
Shuji
S
Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553-0002, Japan.
Komurasaki
Tadafumi
T
Kawada
Kenji
K
Tsuri
Tatsuo
T
Fuji
Masahiro
M
Kugimiya
Akira
A
Haga
Nobuhiro
N
Mitsumori
Susumu
S
Inagaki
Masanao
M
Nakatani
Takuji
T
Tamura
Yoshinori
Y
Takechi
Shozo
S
Taishi
Teruhiko
T
Ohtani
Mitsuaki
M