A new reagent system for installation of an aryl group onto the monoacetate of 4-cyclopentene-1,3-diol

Tetrahedron Letters

Volumn 44, Issue 20, 2003, Pages 3983-3986

  Ainai, Takayuki ^a   Ito, Michiko ^a   Kobayashi, Yuichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

4 cyclopentene 1,3 diol monoacetate; Copper catalyst; Coupling reaction; Dihydromultifidene; Grignard reagent

Indexed keywords

4 CYCLOPENTENE 1,3 DIOL; ACETIC ACID DERIVATIVE; CHEMICAL COMPOUND; DIHYDROMULTIFIDENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; ISOMER; PHENYLATION; SYNTHESIS;

FELIS CATUS;

EID: 0037433807     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00777-9     Document Type: Article

References (41)

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24. 2d are as follows: 2a, 84% yield with a 93:7 ratio; 2b, 82% yield with a 92:8 ratio; 2c, 52% yield with a 88:12 ratio; and 2d, 81% yield with a 90:10 ratio.
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27. Isolation: (a) Boland, W.; Jaenicke, L.; Müller, D. G.; Peters, A. Eur. J. Biochem. 1984, 144, 169-176; (b) Boland, W.; Müller, D. G. Tetrahedron Lett. 1987, 28, 307-310; (c) Maier, I.; Müller, D. G. Z. Naturforsch. 1987, 42c, 948-954; (d) Kajiwara, T.; Hatanaka, A.; Tanaka, Y.; Kawai, T.; Ishihara, M.; Tsuneya, T.; Fujimura, T. Phytochem. 1989, 28, 636-639; (e) Fujimura, T.; Kawai, T.; Kajiwara, T.; Ishida, Y. Plant Tissue Culture Lett. 1994, 11, 34-39; (f) Yamamoto, Y.; Akakabe, Y.; Matsui, K.; Shimizu, H.; Kajiwara, T. Z. Naturforsch. 2000, 56c, 6-12.
28. Isolation: (a) Boland, W.; Jaenicke, L.; Müller, D. G.; Peters, A. Eur. J. Biochem. 1984, 144, 169-176; (b) Boland, W.; Müller, D. G. Tetrahedron Lett. 1987, 28, 307-310; (c) Maier, I.; Müller, D. G. Z. Naturforsch. 1987, 42c, 948-954; (d) Kajiwara, T.; Hatanaka, A.; Tanaka, Y.; Kawai, T.; Ishihara, M.; Tsuneya, T.; Fujimura, T. Phytochem. 1989, 28, 636-639; (e) Fujimura, T.; Kawai, T.; Kajiwara, T.; Ishida, Y. Plant Tissue Culture Lett. 1994, 11, 34-39; (f) Yamamoto, Y.; Akakabe, Y.; Matsui, K.; Shimizu, H.; Kajiwara, T. Z. Naturforsch. 2000, 56c, 6-12.
29. Isolation: (a) Boland, W.; Jaenicke, L.; Müller, D. G.; Peters, A. Eur. J. Biochem. 1984, 144, 169-176; (b) Boland, W.; Müller, D. G. Tetrahedron Lett. 1987, 28, 307-310; (c) Maier, I.; Müller, D. G. Z. Naturforsch. 1987, 42c, 948-954; (d) Kajiwara, T.; Hatanaka, A.; Tanaka, Y.; Kawai, T.; Ishihara, M.; Tsuneya, T.; Fujimura, T. Phytochem. 1989, 28, 636-639; (e) Fujimura, T.; Kawai, T.; Kajiwara, T.; Ishida, Y. Plant Tissue Culture Lett. 1994, 11, 34-39; (f) Yamamoto, Y.; Akakabe, Y.; Matsui, K.; Shimizu, H.; Kajiwara, T. Z. Naturforsch. 2000, 56c, 6-12.
30. Isolation: (a) Boland, W.; Jaenicke, L.; Müller, D. G.; Peters, A. Eur. J. Biochem. 1984, 144, 169-176; (b) Boland, W.; Müller, D. G. Tetrahedron Lett. 1987, 28, 307-310; (c) Maier, I.; Müller, D. G. Z. Naturforsch. 1987, 42c, 948-954; (d) Kajiwara, T.; Hatanaka, A.; Tanaka, Y.; Kawai, T.; Ishihara, M.; Tsuneya, T.; Fujimura, T. Phytochem. 1989, 28, 636-639; (e) Fujimura, T.; Kawai, T.; Kajiwara, T.; Ishida, Y. Plant Tissue Culture Lett. 1994, 11, 34-39; (f) Yamamoto, Y.; Akakabe, Y.; Matsui, K.; Shimizu, H.; Kajiwara, T. Z. Naturforsch. 2000, 56c, 6-12.
31. Isolation: (a) Boland, W.; Jaenicke, L.; Müller, D. G.; Peters, A. Eur. J. Biochem. 1984, 144, 169-176; (b) Boland, W.; Müller, D. G. Tetrahedron Lett. 1987, 28, 307-310; (c) Maier, I.; Müller, D. G. Z. Naturforsch. 1987, 42c, 948-954; (d) Kajiwara, T.; Hatanaka, A.; Tanaka, Y.; Kawai, T.; Ishihara, M.; Tsuneya, T.; Fujimura, T. Phytochem. 1989, 28, 636-639; (e) Fujimura, T.; Kawai, T.; Kajiwara, T.; Ishida, Y. Plant Tissue Culture Lett. 1994, 11, 34-39; (f) Yamamoto, Y.; Akakabe, Y.; Matsui, K.; Shimizu, H.; Kajiwara, T. Z. Naturforsch. 2000, 56c, 6-12.
32. Synthesis: (a) Boland, W.; Mertes, K. Helv. Chim. Acta 1984, 67, 616-624; (b) Wirth, D.; Fischer-Lui, I.; Boland, W.; Icheln, D.; Runge, T.; König, W. A.; Phillips, J.; Clayton, M. Helv. Chim. Acta 1992, 75, 734-744; (c) Kramp, P.; Helmchen, G.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1993, 551-552; (d) Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145-160; (e) Kajiwara, T.; Akakabe, Y.; Matsui, K.; Kodama, K.; Koga, H.; Nagakura, T. Phytochem. 1997, 45, 529-532.
33. Synthesis: (a) Boland, W.; Mertes, K. Helv. Chim. Acta 1984, 67, 616-624; (b) Wirth, D.; Fischer-Lui, I.; Boland, W.; Icheln, D.; Runge, T.; König, W. A.; Phillips, J.; Clayton, M. Helv. Chim. Acta 1992, 75, 734-744; (c) Kramp, P.; Helmchen, G.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1993, 551-552; (d) Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145-160; (e) Kajiwara, T.; Akakabe, Y.; Matsui, K.; Kodama, K.; Koga, H.; Nagakura, T. Phytochem. 1997, 45, 529-532.
34. Synthesis: (a) Boland, W.; Mertes, K. Helv. Chim. Acta 1984, 67, 616-624; (b) Wirth, D.; Fischer-Lui, I.; Boland, W.; Icheln, D.; Runge, T.; König, W. A.; Phillips, J.; Clayton, M. Helv. Chim. Acta 1992, 75, 734-744; (c) Kramp, P.; Helmchen, G.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1993, 551-552; (d) Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145-160; (e) Kajiwara, T.; Akakabe, Y.; Matsui, K.; Kodama, K.; Koga, H.; Nagakura, T. Phytochem. 1997, 45, 529-532.
35. Synthesis: (a) Boland, W.; Mertes, K. Helv. Chim. Acta 1984, 67, 616-624; (b) Wirth, D.; Fischer-Lui, I.; Boland, W.; Icheln, D.; Runge, T.; König, W. A.; Phillips, J.; Clayton, M. Helv. Chim. Acta 1992, 75, 734-744; (c) Kramp, P.; Helmchen, G.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1993, 551-552; (d) Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145-160; (e) Kajiwara, T.; Akakabe, Y.; Matsui, K.; Kodama, K.; Koga, H.; Nagakura, T. Phytochem. 1997, 45, 529-532.
36. Synthesis: (a) Boland, W.; Mertes, K. Helv. Chim. Acta 1984, 67, 616-624; (b) Wirth, D.; Fischer-Lui, I.; Boland, W.; Icheln, D.; Runge, T.; König, W. A.; Phillips, J.; Clayton, M. Helv. Chim. Acta 1992, 75, 734-744; (c) Kramp, P.; Helmchen, G.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1993, 551-552; (d) Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron 1997, 53, 145-160; (e) Kajiwara, T.; Akakabe, Y.; Matsui, K.; Kodama, K.; Koga, H.; Nagakura, T. Phytochem. 1997, 45, 529-532.
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