Total synthesis of terprenin, a novel immunosuppressive p-terphenyl derivative

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5831-5837

  Yonezawa, Shuji ^a   Komurasaki, Tadafumi ^a   Kawada, Kenji ^a   Tsuri, Tatsuo ^a   Fuji, Masahiro ^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   Ohtani, Mitsuaki ^a  

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOGLOBULIN E ANTIBODY; NATURAL PRODUCT; TERPHENYL DERIVATIVE; TERPRENIN; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS; CHEMICAL REACTION; DRUG SYNTHESIS; FERMENTATION;

EID: 15144348175     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980349t     Document Type: Article

References (43)

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2. For our previous work in this field, see: (a) Yasui, K.; Tamura, Y.; Nakatani, T.; Kawada, K.; Ohtani, M. J. Org. Chem. 1995, 60, 7567. (b) Yasui, K.; Tamura, Y.; Nakatani, T.; Horibe, I.; Kawada, K.; Koizumi, K.; Suzuki, R.; Ohtani, M. J. Antibiot. 1996, 49, 173.
3. For our previous work in this field, see: (a) Yasui, K.; Tamura, Y.; Nakatani, T.; Kawada, K.; Ohtani, M. J. Org. Chem. 1995, 60, 7567. (b) Yasui, K.; Tamura, Y.; Nakatani, T.; Horibe, I.; Kawada, K.; Koizumi, K.; Suzuki, R.; Ohtani, M. J. Antibiot. 1996, 49, 173.
4. Only 70 mg of terprenin was isolated from 2 L of the fermentation broth.
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23. For the synthesis of terphenyl compounds, see: (a) Iwema Bakker, W. I.; Haas, M.; den Hertog, H. J., Jr.; Verboom, W.; de Zeeuv, D.; Bruins, A. P.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 972. (b) Todd, M. H.; Balasubramanian, S.; Abell, C. Tetrahedron Lett. 1997, 38, 6781. For recent works in this area, see: (c) Charette, A. B.; Giroux, A. J. Org. Chem. 1996, 61, 8718. (d) Anderson, N. G.; Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1996, 61, 9556. (e) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (f) Su, D. S.; Meng, D.; Bertinato, P.; Balog, A.; Sorenson, E. J.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 757. (g) Ruhland, B.; Bombrun, A.; Gallop, M. A. J. Org. Chem. 1997, 62, 7820.
24. For the synthesis of terphenyl compounds, see: (a) Iwema Bakker, W. I.; Haas, M.; den Hertog, H. J., Jr.; Verboom, W.; de Zeeuv, D.; Bruins, A. P.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 972. (b) Todd, M. H.; Balasubramanian, S.; Abell, C. Tetrahedron Lett. 1997, 38, 6781. For recent works in this area, see: (c) Charette, A. B.; Giroux, A. J. Org. Chem. 1996, 61, 8718. (d) Anderson, N. G.; Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1996, 61, 9556. (e) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (f) Su, D. S.; Meng, D.; Bertinato, P.; Balog, A.; Sorenson, E. J.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 757. (g) Ruhland, B.; Bombrun, A.; Gallop, M. A. J. Org. Chem. 1997, 62, 7820.
25. For the synthesis of terphenyl compounds, see: (a) Iwema Bakker, W. I.; Haas, M.; den Hertog, H. J., Jr.; Verboom, W.; de Zeeuv, D.; Bruins, A. P.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 972. (b) Todd, M. H.; Balasubramanian, S.; Abell, C. Tetrahedron Lett. 1997, 38, 6781. For recent works in this area, see: (c) Charette, A. B.; Giroux, A. J. Org. Chem. 1996, 61, 8718. (d) Anderson, N. G.; Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1996, 61, 9556. (e) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (f) Su, D. S.; Meng, D.; Bertinato, P.; Balog, A.; Sorenson, E. J.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 757. (g) Ruhland, B.; Bombrun, A.; Gallop, M. A. J. Org. Chem. 1997, 62, 7820.
26. For the synthesis of terphenyl compounds, see: (a) Iwema Bakker, W. I.; Haas, M.; den Hertog, H. J., Jr.; Verboom, W.; de Zeeuv, D.; Bruins, A. P.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 972. (b) Todd, M. H.; Balasubramanian, S.; Abell, C. Tetrahedron Lett. 1997, 38, 6781. For recent works in this area, see: (c) Charette, A. B.; Giroux, A. J. Org. Chem. 1996, 61, 8718. (d) Anderson, N. G.; Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1996, 61, 9556. (e) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (f) Su, D. S.; Meng, D.; Bertinato, P.; Balog, A.; Sorenson, E. J.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 757. (g) Ruhland, B.; Bombrun, A.; Gallop, M. A. J. Org. Chem. 1997, 62, 7820.
27. For the synthesis of terphenyl compounds, see: (a) Iwema Bakker, W. I.; Haas, M.; den Hertog, H. J., Jr.; Verboom, W.; de Zeeuv, D.; Bruins, A. P.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 972. (b) Todd, M. H.; Balasubramanian, S.; Abell, C. Tetrahedron Lett. 1997, 38, 6781. For recent works in this area, see: (c) Charette, A. B.; Giroux, A. J. Org. Chem. 1996, 61, 8718. (d) Anderson, N. G.; Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1996, 61, 9556. (e) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (f) Su, D. S.; Meng, D.; Bertinato, P.; Balog, A.; Sorenson, E. J.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 757. (g) Ruhland, B.; Bombrun, A.; Gallop, M. A. J. Org. Chem. 1997, 62, 7820.
28. For the synthesis of terphenyl compounds, see: (a) Iwema Bakker, W. I.; Haas, M.; den Hertog, H. J., Jr.; Verboom, W.; de Zeeuv, D.; Bruins, A. P.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 972. (b) Todd, M. H.; Balasubramanian, S.; Abell, C. Tetrahedron Lett. 1997, 38, 6781. For recent works in this area, see: (c) Charette, A. B.; Giroux, A. J. Org. Chem. 1996, 61, 8718. (d) Anderson, N. G.; Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1996, 61, 9556. (e) Sengupta, S.; Bhattacharyya, S. J. Org. Chem. 1997, 62, 3405. (f) Su, D. S.; Meng, D.; Bertinato, P.; Balog, A.; Sorenson, E. J.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 757. (g) Ruhland, B.; Bombrun, A.; Gallop, M. A. J. Org. Chem. 1997, 62, 7820.
29. For a palladium-catalyzed hydrogenolysis of allylic compounds, see: Tsuji, J.; Mandai, T. Synthesis 1996, 1.
30. 2O for 1 h at 25 °C.
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36. Efforts to effect the iododethallation of 2 were unrewarding. For related iodination reactions, see: (a) Taylor, E. C.; Kienzle, F.; Robey, R. L.; McKillop, A.; Hunt, J. D. J. Am. Chem. Soc. 1971, 93, 4845. (b) Merkushev, E. B. Synthesis 1988, 923. (c) Noda, Y.; Kashima, M. Tetrahedron Lett. 1997, 38, 6225. (d) Zupan, M.; Iskra, J.; Stavber, S. Tetrahedron Lett. 1997, 38, 6305.
37. Efforts to effect the iododethallation of 2 were unrewarding. For related iodination reactions, see: (a) Taylor, E. C.; Kienzle, F.; Robey, R. L.; McKillop, A.; Hunt, J. D. J. Am. Chem. Soc. 1971, 93, 4845. (b) Merkushev, E. B. Synthesis 1988, 923. (c) Noda, Y.; Kashima, M. Tetrahedron Lett. 1997, 38, 6225. (d) Zupan, M.; Iskra, J.; Stavber, S. Tetrahedron Lett. 1997, 38, 6305.
38. Efforts to effect the iododethallation of 2 were unrewarding. For related iodination reactions, see: (a) Taylor, E. C.; Kienzle, F.; Robey, R. L.; McKillop, A.; Hunt, J. D. J. Am. Chem. Soc. 1971, 93, 4845. (b) Merkushev, E. B. Synthesis 1988, 923. (c) Noda, Y.; Kashima, M. Tetrahedron Lett. 1997, 38, 6225. (d) Zupan, M.; Iskra, J.; Stavber, S. Tetrahedron Lett. 1997, 38, 6305.
39. Efforts to effect the iododethallation of 2 were unrewarding. For related iodination reactions, see: (a) Taylor, E. C.; Kienzle, F.; Robey, R. L.; McKillop, A.; Hunt, J. D. J. Am. Chem. Soc. 1971, 93, 4845. (b) Merkushev, E. B. Synthesis 1988, 923. (c) Noda, Y.; Kashima, M. Tetrahedron Lett. 1997, 38, 6225. (d) Zupan, M.; Iskra, J.; Stavber, S. Tetrahedron Lett. 1997, 38, 6305.
40. For the iodination of phenols with iodine and amines, see: (a) Chabrier, P.; Seyden-Penne, J.; Fouace, A. C. R. Acad. Sci. 1957, 245, 174. For related ortho-bromination of phenols, see: (b) Pearson, D. E.; Wysong, R. D.; Breder, C. V. J. Org. Chem. 1967, 32, 2358. (c) Fujisaki, S.; Eguchi, H.; Omura, A.; Okamoto, A.; Nishida, A. Bull. Chem. Soc. Jpn. 1993, 66, 1576.
41. For the iodination of phenols with iodine and amines, see: (a) Chabrier, P.; Seyden-Penne, J.; Fouace, A. C. R. Acad. Sci. 1957, 245, 174. For related ortho-bromination of phenols, see: (b) Pearson, D. E.; Wysong, R. D.; Breder, C. V. J. Org. Chem. 1967, 32, 2358. (c) Fujisaki, S.; Eguchi, H.; Omura, A.; Okamoto, A.; Nishida, A. Bull. Chem. Soc. Jpn. 1993, 66, 1576.
42. For the iodination of phenols with iodine and amines, see: (a) Chabrier, P.; Seyden-Penne, J.; Fouace, A. C. R. Acad. Sci. 1957, 245, 174. For related ortho-bromination of phenols, see: (b) Pearson, D. E.; Wysong, R. D.; Breder, C. V. J. Org. Chem. 1967, 32, 2358. (c) Fujisaki, S.; Eguchi, H.; Omura, A.; Okamoto, A.; Nishida, A. Bull. Chem. Soc. Jpn. 1993, 66, 1576.
43. 3 as the catalyst.