Total synthesis of cyclostellettamine C, a bispyridinium macrocyclic alkaloid having muscarinic acetylcholine receptor antagonistic activity

Tetrahedron

Volumn 52, Issue 33, 1996, Pages 10849-10860

  Anan, Hideki ^a   Seki, Norio ^a   Noshiro, Osamu ^a   Honda, Kazuo ^a   Yasumuro, Kenichi ^a   Ozasa, Teruaki ^a   Fusetani, Nobuhiro ^b  

^a ASTELLAS PHARMA INC   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYCLOSTELLETTAMINE C; MUSCARINIC RECEPTOR; MUSCARINIC RECEPTOR BLOCKING AGENT; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BRAIN; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HEART; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; RAT; REACTION ANALYSIS; SALIVARY GLAND;

ANIMALIA;

EID: 0030581344     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00628-X     Document Type: Article

References (14)

1. 1. Schmitz, F. J.; Hollenbeak, K. H.; Campbell, D. C. J. Org. Chem. 1978, 43, 3916-3922. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hirota, H. Tetrahedron Lett. 1989, 30, 6891-1894. Talpir, R.; Rudi, A.; Ilan, M.; Kashman, Y. Tetrahedron Lett. 1992, 33, 3033-3034.
2. 1. Schmitz, F. J.; Hollenbeak, K. H.; Campbell, D. C. J. Org. Chem. 1978, 43, 3916-3922. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hirota, H. Tetrahedron Lett. 1989, 30, 6891-1894. Talpir, R.; Rudi, A.; Ilan, M.; Kashman, Y. Tetrahedron Lett. 1992, 33, 3033-3034.
3. 1. Schmitz, F. J.; Hollenbeak, K. H.; Campbell, D. C. J. Org. Chem. 1978, 43, 3916-3922. Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hirota, H. Tetrahedron Lett. 1989, 30, 6891-1894. Talpir, R.; Rudi, A.; Ilan, M.; Kashman, Y. Tetrahedron Lett. 1992, 33, 3033-3034.
4. 2. Fusetani, N.; Asai, N.; Matsunaga, S.; Honda, K.; Yasumuro, K. Tetrahedron Lett. 1994, 35, 3967-3970.
5. 3. Davies-Coleman, M. T.; Faulkner, D. J.; Dubowchik, G. M.; Roth, G. P.; Poison, C.; Fairchild, C. J. Org. Chem. 1993, 58, 5925-5930.
6. 4. Classon, B.; Liu, Z.; Samuelsson, B. J. Org. Chem. 1988, 53, 6126-6130.
7. - ratio of 1/1.
8. 6. Other more polar products were produced as inseparable mixtures but they were not characterized.
9. 7. Jung, M. E.; Lyster, M. A. J. Org. Chem. 1977, 42, 3761-3764.
10. 8. 8 was stable under the acidic conditions (3N HCl aqueous EtOH at 80 °C overnight), but hydrogenation on Pd/C (existence of a catalytic amount of HCI) gave a polar and nonfluorescent product.
11. 2.
12. 10. Yazawa, H.; Honda, K. Japan. J. Pharmacol. 1993, 61, 319-324.
13. 11. Wess, J. Trends Pharmacol. Sci., 1993, 14, 308-313.
14. 12. Benzyliodide, which was produced over this reaction, was trapped as BnNHMe to prevent reaction with the pyridine moiety of the required product and to facilitate separation.