Total synthesis of terprenin, a highly potent and novel immunoglobulin E antibody suppressant

Angewandte Chemie - International Edition

Volumn 37, Issue 7, 1998, Pages 973-975

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

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

Cross coupling; Immunosuppressants; Natural products; Terprenin; Total synthesis

Indexed keywords

EID: 0031971526     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980420)37:7<973::AID-ANIE973>3.0.CO;2-T     Document Type: Article

References (14)

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3. Although splatast has been approved recently in Japan as an antiallergic drug with a suppressive effect on IgE production, its clinical effect remains obscure.
4. Fermentation, isolation, and structure determination: T. Kamigauchi, R. Sakazaki, K. Nagashima, Y. Kawamura, Y. Yasuda, K. Matsushima, H. Tani, Y. Takahashi, K. Ishii, R. Suzuki, K. Koizumi, H. Nakai, Y. Ikenishi, Y. Terui, J. Antibiot., submitted.
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8. 2O for 1 h at 25°C.
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10. A similar reaction has been reported recently: see N. S. Wilson, B. A. Keay, Tetrahedron Lett. 1996, 37, 153-156.
11. Synthesis of 14: a) U. Schmidt, R. Meyer, V. Leitenberger, H. Griesser, A. Lieberknecht, Synthesis 1992, 1025-1030; b) K. Suzuki, N. Satake, A. Sugiura, T. Fujii (Kanto Kagaku), JP-B 5-213930, 1993 [Chem. Abstr. 1994, 120, 134493 t].
12. Synthesis of 14: a) U. Schmidt, R. Meyer, V. Leitenberger, H. Griesser, A. Lieberknecht, Synthesis 1992, 1025-1030; b) K. Suzuki, N. Satake, A. Sugiura, T. Fujii (Kanto Kagaku), JP-B 5-213930, 1993 [Chem. Abstr. 1994, 120, 134493 t].
13. For related ortho-bromination of phenols, see a) D. E. Pearson, R. D. Wysong, C. V. Breder, J. Org. Chem. 1967, 32, 2358-2360; b) S. Fujisaki, H. Eguchi, A. Omura, A. Okamoto, A. Nishida, Bull. Chem. Soc. Jpn. 1993, 66, 1576-1579.
14. For related ortho-bromination of phenols, see a) D. E. Pearson, R. D. Wysong, C. V. Breder, J. Org. Chem. 1967, 32, 2358-2360; b) S. Fujisaki, H. Eguchi, A. Omura, A. Okamoto, A. Nishida, Bull. Chem. Soc. Jpn. 1993, 66, 1576-1579.