Total Synthesis of Terprenin, a Highly Potent and Novel Immunoglobulin E Antibody Suppressant

Kenji Kawada; Akinori Arimura; Tatsuo Tsuri; Masahiro Fuji; Tadafumi Komurasaki; Shuji Yonezawa; Akira Kugimiya; Nobuhiro Haga; Susumu Mitsumori; Masanao Inagaki; Takuji Nakatani; Yoshinori Tamura; Shozo Takechi; Teruhiko Taishi; Junji Kishino; Mitsuaki Ohtani

doi:10.1002/(SICI)1521-3773(19980420)37:7<973::AID-ANIE973>3.0.CO;2-T

Total Synthesis of Terprenin, a Highly Potent and Novel Immunoglobulin E Antibody Suppressant

Angew Chem Int Ed Engl. 1998 Apr 20;37(7):973-975. doi: 10.1002/(SICI)1521-3773(19980420)37:7<973::AID-ANIE973>3.0.CO;2-T.

Authors

Kenji Kawada¹, Akinori Arimura¹, Tatsuo Tsuri¹, Masahiro Fuji¹, Tadafumi Komurasaki¹, Shuji Yonezawa¹, Akira Kugimiya¹, Nobuhiro Haga¹, Susumu Mitsumori¹, Masanao Inagaki¹, Takuji Nakatani¹, Yoshinori Tamura¹, Shozo Takechi¹, Teruhiko Taishi¹, Junji Kishino¹, Mitsuaki Ohtani¹

Affiliation

¹ Shionogi Research Laboratories, Shionogi & Co., Ltd., Fukushima-ku, Osaka 553 (Japan), Fax: (+81) 6-458-0987.

PMID: 29711491
DOI: 10.1002/(SICI)1521-3773(19980420)37:7<973::AID-ANIE973>3.0.CO;2-T

Abstract

Regioselective halogenations and Suzuki reactions ensure proper linkage of the aromatic rings in two total syntheses of terprenin (1). Both routes make it possible to prepare 1 efficiently and in large quantity.

Keywords: Cross-coupling; Immunosuppressants; Natural products; Terprenin; Total synthesis.