A Short Synthesis of Phenyl Kainoid

Synlett

Volumn 1996, Issue 1, 1996, Pages 95-96

  Horikawa, Manabu ^a,b   Shirahama, Haruhisa ^a,c  

^a HOKKAIDO UNIVERSITY   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

^c KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002288740     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5333     Document Type: Article

References (33)

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15. h) Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. Other group's syntheses: Reviews; Hashimoto, K.; Shirahama, H. Trends in Organic Chemistry-2; Karma, V., Ed.; Research Trends, Trivandrum, India, 1991, p1. Recent syntheses: Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1991, 47, 155.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1991, 47, 3451. Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem. Soc., Chem. Commun. 1991, 390. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. Yoo, S-E.; Lee, S-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163.
16. h) Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. Other group's syntheses: Reviews; Hashimoto, K.; Shirahama, H. Trends in Organic Chemistry-2; Karma, V., Ed.; Research Trends, Trivandrum, India, 1991, p1. Recent syntheses: Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1991, 47, 155.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1991, 47, 3451. Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem. Soc., Chem. Commun. 1991, 390. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. Yoo, S-E.; Lee, S-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163.
17. h) Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. Other group's syntheses: Reviews; Hashimoto, K.; Shirahama, H. Trends in Organic Chemistry-2; Karma, V., Ed.; Research Trends, Trivandrum, India, 1991, p1. Recent syntheses: Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1991, 47, 155.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1991, 47, 3451. Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem. Soc., Chem. Commun. 1991, 390. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. Yoo, S-E.; Lee, S-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163.
18. h) Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. Other group's syntheses: Reviews; Hashimoto, K.; Shirahama, H. Trends in Organic Chemistry-2; Karma, V., Ed.; Research Trends, Trivandrum, India, 1991, p1. Recent syntheses: Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1991, 47, 155.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1991, 47, 3451. Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem. Soc., Chem. Commun. 1991, 390. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. Yoo, S-E.; Lee, S-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163.
19. h) Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. Other group's syntheses: Reviews; Hashimoto, K.; Shirahama, H. Trends in Organic Chemistry-2; Karma, V., Ed.; Research Trends, Trivandrum, India, 1991, p1. Recent syntheses: Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1991, 47, 155.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1991, 47, 3451. Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem. Soc., Chem. Commun. 1991, 390. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. Yoo, S-E.; Lee, S-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163.
20. h) Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. Other group's syntheses: Reviews; Hashimoto, K.; Shirahama, H. Trends in Organic Chemistry-2; Karma, V., Ed.; Research Trends, Trivandrum, India, 1991, p1. Recent syntheses: Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1991, 47, 155.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1991, 47, 3451. Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem. Soc., Chem. Commun. 1991, 390. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. Yoo, S-E.; Lee, S-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163.
21. h) Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. Other group's syntheses: Reviews; Hashimoto, K.; Shirahama, H. Trends in Organic Chemistry-2; Karma, V., Ed.; Research Trends, Trivandrum, India, 1991, p1. Recent syntheses: Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1991, 47, 155.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1991, 47, 3451. Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem. Soc., Chem. Commun. 1991, 390. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. Yoo, S-E.; Lee, S-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163.
22. h) Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799. Other group's syntheses: Reviews; Hashimoto, K.; Shirahama, H. Trends in Organic Chemistry-2; Karma, V., Ed.; Research Trends, Trivandrum, India, 1991, p1. Recent syntheses: Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1991, 47, 155.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1991, 47, 3451. Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem. Soc., Chem. Commun. 1991, 390. Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1992, 553. Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169. Yoo, S-E.; Lee, S-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125. Baldwin, J. E.; Rudolph, M. Tetrahedron Lett. 1994, 35, 6163.
23. 6f
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29. 3), 57.41 (0.5×5H, s), 7.40 (0.5×5H, s), 4.41 (0.5×1H, d, J = 4.9 Hz), 4.25 (0.5×1H, d, J = 4.9 Hz), 4.29 (0.5×1H, d, J = 13.2 Hz), 4.23 (0.5×1H, d, J = 13.2 Hz), 3.90 (0.5×1H, d, J = 13.2 Hz), 3.88 (0.5×1H, d, J = 13.2 Hz), 3.84 (3H, s), 3.19 (1H, ddd, J = 4.9, 8.3, 12.7 Hz), 2.83 (1.5×1H, dd, J = 8.3, 18.1 Hz), 2.78 (0.5×1H, dd, J = 8.3, 18.1 Hz), 2.70 (1H, dd, J = 12.7, 18.1 Hz), 1.46 (0.5×9H, s), 1.44 (0.5×9H, s). This spectrum showed the existence of two conformer probably due to restricted rotation of the N-Boc bond.
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33. + 250.1079, found 250.1060.