Absolute configuration of norzoanthamine, a promising candidate for an osteoporotic drug

Tetrahedron Letters

Volumn 38, Issue 32, 1997, Pages 5683-5686

  Kuramoto, Makoto ^c   Hayashi, Koji ^b   Fujitani, Yasuyuki ^b   Yamaguchi, Kohji ^a   Tsuji, Tomoko ^a   Yamada, Kaoru ^a   Ijuin, Yasuharu ^a   Uemura, Daisuke ^b  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b SHIZUOKA UNIVERSITY   (Japan)

^c EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; NORZOANTHAMINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0030761991     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01238-0     Document Type: Article

References (15)

1. Dedicated to Prof. Yoshito Kishi on the occasion of his 60th birthday.
2. Fukuzawa, S.; Hayashi, Y.; Uemura, D.; Nagastu, A.; Yamada, K.; Ijyuin, Y. Heterocycl. Commun., 1995, 1, 207.
3. a) Rao, C. B.; Anjaneyula, A. S. R.; Sarma, N. S.; Venkatateswarlu, Y.; Rosser, R. M.; Faulkner, D. J.; Chen, M. H. M.; Clardy, J. J. Am. Chem. Soc., 1984, 106, 7983.
4. b) Rao, C. B.; Anjaneyula, A. S. R.; Sarma, N. S.; Venkatateswarlu, Y.; Rosser, R. M.; Faulkner, D. J.; Chen, M. H. M.; Clardy, J. J. Org. Chem., 1985, 50, 3757.
5. c)Rao, C. B.; Rao, D. V.; Raju, V. S. N.; Sullivan, B. W.; Faulkner, D. J. Heterocycles, 1989, 28, 103.
6. d) Atta-ur-Rahman, Alvi, K. A.; Abbas, S. A.; Choudhary, M. I.; Clardy, J. Tetrahedron Lett. ,1989, 30, 6825.
7. Kuramoto, M.; Arimoto, H.; Hayashi, K.; Hayakawa, I.; Uemura, D.; Chou, T.; Yamada, K.; Tsuji, T.; Yamaguchi, K.; Yazawa, K. Symposium Papers, 38th Symposium on the Chemistry of Natural Products, 79-84 (1996).
8. NMR spectra were recorded on a JNM-GSX 400 spectrometer.
9. Mass spectra were recorded on a M-80B mass spectrometer.
10. 3).
11. 3; δ 60.1 (C-1), 72.2 (C-2), 37.9 (C-3), 23.3 (C-4), 44.6 (C-5), 92.4 (C-6), 54.7 (C-7), 33.6 (C-8), 36.3 (C-9), 71.1 (C-10), 36.4 (C-11), 41.2 (C-12), 53.5 (C-13), 31.3 (C-14), 160.0 (C-15), 125.5 (C-16), 198.7 (C-17), 45.5 (C-18), 43.0 (C-19), 209.0 (C-20), 62.2 (C-21), 41.1 (C-22), 47.1 (C-23), 211.5 (C-24), 22.7 (C-25), 24.2 (C-26), 17.7 C-27), 24.0 (C-28), 21.7 (C-29).
12. Quite recently, we performed an X-ray crystallographic analysis of 2 itself. Detailed data will be reported elsewhere.
13. 3: δ 60.1 (C-1), 71.1 (C-2), 37.8(C-3), 23.2 (C-4), 44.5 (C-5), 92.5 (C-6), 54.7 (C-7), 33.6 (C-8), 36.1 (C-9), 71.1 (C-10), 36.1 (C-11), 41.2 (C-12), 50.8 (C-13), 29.4 (C-14), 133.0 (C-15), 124.8 (C-16), 75.2 (C-17), 42.5 (C-18), 47.5 (C-19), 210.0 (C-20), 62.0 (C-21), 41.1 (C-22), 47.1 (C-23), 212.0 (C-24), 22.8 (C-25), 23.3 (C-26), 17.3 C-27), 24.1 (C-28), 21.8 (C-29).
14. H 2.04 ppm).
15. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc., 1991, 113, 4092.