Studies on disease-modifying antirheumatic drugs. III. Bone resorption inhibitory effects of ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-(1,2,4- triazol-1-ylmethyl)quinoline-3-carboxylate (TAK-603) and related compounds

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 3, 1999, Pages 369-374

  Baba, Atsuo ^a   Oda, Tsuneo ^a   Taketomi, Shigehisa ^a   Notoya, Kohei ^a   Nishimura, Atsushi ^a   Makino, Haruhiko ^a   Sohda, Takashi ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

Antiresorptive activity; Bone and joint disease; Bone resorption; Justicidin; TAK 603

Indexed keywords

4 (3,4 DIMETHOXYPHENYL) 6,7 DIMETHOXY 2 (1,2,4 TRIAZOL 1 YLMETHYL) 3 QUINOLINECARBOXYLIC ACID ETHYL ESTER; ANTIRHEUMATIC AGENT; JUSTICIDIN; LACTONE; PYRROLE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BONE; BONE ATROPHY; BONE METABOLISM; CONTROLLED STUDY; DRUG EFFECT; DRUG EFFICACY; DRUG POTENCY; FEMALE; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; OSTEOCLAST; OSTEOLYSIS;

EID: 0032926626     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.369     Document Type: Article

References (43)

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14. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
15. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
16. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
17. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
18. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
19. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
20. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
21. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
22. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
23. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
24. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
25. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
26. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
27. Synthesis of this type of naphthalene lactone was reported by several groups: a) Arnold B. J., Mellows S. M., Sammes P. G., J. Chem. Soc., Perkin Trans 1, 1973, 1266-1270; b) Horii Z., Tsujiuchi M., Kanai K., Momose T., Chem. Pharm Bull., 25, 1803-1808 (1977); c) Momose T., Kanai K., Hayashi K., ibid., 26, 3195-3198 (1978); d) Silva S. O., Denis C. S., Rodrigo R., J. Chem. Soc., Chem. Comm., 1980, 995-997; e) Mann J., Piper S. E., Yeung L. K. P., J. Chem. Soc., Perkin Trans. 1, 1984, 2081-2088; f) Takano S., Otaki S., Ogasawara K., Tetrahedron Lett., 26, 1659-1660 (1985); g) Ishii Y., Ikariya T,. Saburi M., Yoshikawa S., ibid., 27, 365-368 (1986); h) Seko S., Tanabe Y., Suzukamo G., ibid., 31, 6883-6886 (1990); i) Ogiku T., Seki M., Takahashi M., Ohmizu H., Iwasaki T., ibid., 31, 5487-5490 (1990); j) Kobayashi K., Kanno Y., Seko S., Suginome H., J. Chem. Soc., Perkin Trans 1, 1992, 3111-3117; k) Hattori T., Tanaka H., Okashi Y., Miyano S., ibid. 1995, 235-241. l) Ogiku T., Yoshida S., Ohmizu H., Iwasaki T., J. Org. Chem., 60, 4585-4590 (1995); m) Tanabe Y., Seko S., Nishii Y., Yoshida T., Utsumi N., Suzukamo G., J. Chem. Soc., Perkin Trans 1, 1996, 2157-2165. n) Padwa A., Cochran J. E., Kappe C. O., J. Org. Chem., 61, 3706-3714 (1996).
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