Total Synthesis of Terprenin, a Novel Immunosuppressive p-Terphenyl Derivative
The Journal of Organic Chemistry1998Vol. 63(17), pp. 5831–5837
Citations Over Time
Shuji Yonezawa, Tadafumi Komurasaki, Kenji Kawada, Tatsuo Tsuri, Masahiro Fuji, Akira Kugimiya, Nobuhiro Haga, Susumu Mitsumori, Masanao Inagaki, Takuji Nakatani, Yoshinori Tamura, Shozo Takechi, Teruhiko Taishi, Mitsuaki Ohtani
Abstract
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.
Related Papers
- → Concise Total Synthesis and Stereochemical Revision of (+)-Naseseazines A and B: Regioselective Arylative Dimerization of Diketopiperazine Alkaloids(2011)155 cited
- → Chemoenzymatic Total Synthesis of the Phytotoxic Geranylcyclohexentriol (−)-Phomentrioloxin(2013)29 cited
- → Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A(1996)53 cited
- → Asymmetric total synthesis of reported structure of eudistomidin B, an indole alkaloid isolated from a marine tunicate(2009)30 cited
- → Structural incongruities of coleophomone natural products: insights by total synthesis of a semi-synthetic derivative(2003)20 cited