New procedure to mask the 2,3-π bond of the indole nucleus and its application to the preparation of potent opioid receptor agonists with a corynanthe skeleton

Organic Letters

Volumn 8, Issue 25, 2006, Pages 5705-5708

  Takayama, Hiromitsu ^a   Misawa, Kaori ^a   Okada, Naoki ^a   Ishikawa, Hayato ^a   Kitajima, Mariko ^a   Hatori, Yoshio ^a   Murayama, Toshihiko ^a   Wongseripipatana, Sumphan ^b   Tashima, Kimihito ^c   Matsumoto, Kenjiro ^c   Horie, Syunji ^c  

^a CHIBA UNIVERSITY   (Japan)

^b CHULALONGKORN UNIVERSITY   (Thailand)

^c JOSAI INTERNATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CORYNANTHE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ETHYLENE GLYCOL; INDOLE DERIVATIVE; IODINE; OPIATE RECEPTOR; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; DRUG POTENTIATION; GUINEA PIG; ILEUM; IN VITRO STUDY; MITRAGYNA; MUSCLE CONTRACTION; SMOOTH MUSCLE; SYNTHESIS;

ALKALOIDS; ANIMALS; ETHYLENE GLYCOL; GUINEA PIGS; ILEUM; INDICATORS AND REAGENTS; INDOLES; IODINE; MITRAGYNA; MUSCLE CONTRACTION; MUSCLE, SMOOTH; PYRROLES; RECEPTORS, OPIOID;

EID: 33846304653     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062173k     Document Type: Article

References (22)

1. Ponglux, D.; Wongseripipatana, S.; Takayama, H.; Kikuchi, M.; Kurihara, M.; Kitajima, M.; Aimi, N.; Sakai, S. Planta Med. 1994, 60, 580-581.
2. (a) Takayama, H. Chem. Pharm. Bull. 2004, 52, 916-928.
3. (b) Takayama, H.; Kitajima, M.; Kogure, N. Curr. Org. Chem. 2005, 9, 1445-1464.
4. (c) Takayama, H.; Kurihara, M.; Kitajima, M.; Said, I. M.; Aimi, N. J. Org. Chem. 1999, 64, 1772-1773.
5. (d) Takayama, H.; Ishikawa, H.; Kurihara, M.; Kitajima, M.; Sakai, S.; Aimi, N.; Seki, H.; Yamaguchi, K.; Said, I. M.; Houghton, P. J. Tetrahedron Lett. 2001, 42, 1741-1743.
6. Takayama, H.; Ishikawa, H.; Kurihara, M.; Kitajima, M.; Aimi, N.; Ponglux, D.; Koyama, F.; Matsumoto, K.; Moriyama, T.; Yamamoto, L. T.; Watanabe, K.; Murayama, T.; Horie, S. J. Med. Chem. 2002, 45, 1949-1956.
7. 7-Hydroxymitragynine (1) has an advantage over morphine when administered orally because morphine is not so effective when administered orally. Matsumoto, K.; Horie, S.; Ishikawa, H.; Takayama, H.; Aimi, N.; Ponglux, D.; Watanabe, K. Life Sci. 2004, 74, 2143-2155.
8. Matsumoto, K.; Horie, S.; Takayama, H.; Ishikawa, H.; Aimi, N.; Ponglux, D.; Murayama, T.; Watanabe, K. Life Sci. 2005, 78, 2-7.
9. Matsumoto, K.; Hatori, Y.; Murayama, T.; Tashima, K.; Wongseripipatana, S.; Misawa, K.; Kitajima, M.; Takayama, H.; Horie, S. Eur. J. Pharmacol. Available online 16 August 2006.
10. (a) Takayama, H.; Maeda, M.; Ohbayashi, S.; Kitajima, M.; Sakai, S.; Aimi, N. Tetrahedron Lett. 1995, 36, 9337-9340.
11. (b) Matsumoto, K.; Mizowaki, M.; Suchitra, T.; Takayama, H.; Sakai, S.; Aimi, N.; Watanabe, H. Life Sci. 1996, 59, 1149-1155.
12. A method for protection-deprotection of the indole 2,3-bond using MTDA was reported. (a) Baran, P. S.; Guerrero, C. A.; Corey, E. J. Org. Lett. 2003, 5, 1999-2001.
13. (b) Baran, P. S.; Guerrero, C. A.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 5628-5629.
14. (a) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656-3665.
15. (b) Moriarty, R. M. J. Org. Chem. 2005, 70, 2893-2903.
16. (c) Dohi, T.; Morimoto, K.; Maruyama, A.; Kita, Y. Org. Lett. 2006, 8, 2007-2010 and references cited therein.
17. 4Cl method. The reaction mechanism for the formation of EG adducts with hypervalent iodines is still unclear.
18. The preparation of various A-ring-modified reserpines will be published in due course.
19. Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563-8575.
20. Mellor, J. M.; Mittoo, S.; Parkes, R.; Miller, R. W. Tetrahedron 2000, 56, 8019-8024.
21. Magnus, P.; Gazzard, L.; Hobson, L.; Payne, A. H.; Rainey, T. J.; Westlund, N.; Lynch, V. Tetrahedron 2002, 58, 3423-3443.
22. Ishikawa, H.; Takayama, H.; Aimi, N. Tetrahedron Lett. 2002, 43, 5637-5639.