Modifications of Norditerpenoid Alkaloids: I. N-Deethylation Reactions

Chinese Chemical Letters

Volumn 10, Issue 5, 1999, Pages 375-378

  Wang, Feng Peng ^a   Fan, Ju Zheng ^a   Li, Zheng Bang ^a   Yang, Jin Song ^a   Li, Bo Gang ^b  

^a SCHOOL OF BASIC MEDICAL SCIENCES   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

N deethylation; Norditerpenpid alkaloids

Indexed keywords

EID: 0033454983     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. a). M. H. Benn and J .M. Jacyno, The toxicology and pharmacology of diterpenoid alkaloids, in "The Alkaloids: Chemical and Biological Perspectives" (S. W. Pelletier, ed.), vol. 1, pp. 153-210, John Wiley & Sons, New York, 1983;
2. b). F. N. Dzhakhangirov, M. N. Sultankhodzhaev, B. Tashkhodzhaev, and B. T. Silimov, Khim. Prir. Soedin, 1997, 33, 254-270.
3. a). F. P. Wang and X. T. Liang, Chemistry of the diterpenoid alkaloids, in "The Alkaloids: Chemistry and Pharmacology" (G. A. Cordell, ed.), vol. 42, Academic Press, pp. 152-247;
4. b). S. W. Pelletier, J. Nat. Prod, 1992, 55, 1-24;
5. c). Feng Peng WANG, Youji Huaxue, 1994, 14, 359-369.
6. F. P. Wang and S. W. Pelletier, West China J. Pharm. Sci, 1989, 4, 193.
7. F. P. Wang, C. S. Peng, Z. B. Li, Phytochemistry, submitted.
8. +, 13), 406 (88), 390 (49), 378 (100).
9. +, 9), 420 (19), 404 (100), 376 (34).
10. 13C NMR (50MHz) δ: 84.5 (1), 24.2 (2), 27.5 (3), 46.3 (4), 55.2 (5), 215.3 (6), 61.4 (7), 81.3 (8), 56.0 (9), 45.9 (10), 48.7 (11), 25.8 (12), 44.9 (13), 211.8 (14), 34.9 (15), 82.8 (16), 66.4 (17), 73.9 (18), 165.5 (19), 55.9 (1′), 56.2 (16′), 59.3 (18′).
11. +, 10), 71 (100).
12. +, 6), 504 (M-31, 100), 444 (38).
13. +, 10), 415 (72), 135 (100).
14. 3).
15. O. Achmatowicz. JR., Y. Tsuda, and L. Marion, Can. J. Chem, 1965, 43, 2336.
16. 13C NMR (50MHz) δ: 79.9 (1), 29.7 (2), 69.5 (3), 42.6 (4), 42.4 (5), 81.6 (6), 50.9 (7), 84.2 (8), 43.1 (9), 39.0 (10), 49.7 (11), 28.0 (12), 43.3 (13), 75.1 (14), 37.4 (15), 82.4 (16), 59.1 (17), 76.8 (18), 41.1 (19), 55.2 (1′), 57.5 (6′), 56.8 (16′), 58.3 (18′).
17. 13C NMR (50MHz) δ: 80.0 (1), 34.9 (2), 71.0 (3), 43.8 (4), 51.4 (5), 83.4 (6), 43.6 (7), 84.3 (8), 47.3 (9), 41.0 (10), 49.4 (11), 34.9 (12), 74.1 (13), 78.9 (14), 37.4 (15), 82.4 (16), 61.0 (17), 77.6 (18), 40.7 (19), 55.7 (1′), 57.6 (6′), 56.8 (16′), 59.1 (18′), 168.9, 21.3 (OAc), 166.0 (O=C-O), 129.8 (1″), 129.5 (2″, 6″), 128.6 (3″, 5″), 133.4 (4″).
18. 13C NMR (100MHz) δ: 80.6 (1), 30.3 (2), 71.8 (3), 42.5 (4), 57.2 (5), 81.9 (6), 49.0 (7), 73.3 (8), 45.1 (9), 41.1 (10), 49.1 (11), 35.0 (12), 76.3 (13), 78.9 (14), 40.9 (15), 83.1 (16), 58.9 (17), 74.2 (18), 41.3 (19), 55.6 (1′), 57.7 (6′), 58.0 (16′), 59.0 (18′), 170.0, 21.1 (OAc). FABMS m/z(%): 498 ((M+1), 100).
19. F. P. Wang, Z. B. Li, J. S. Yang and B. G. Li, Chin. Chem. Lett, submitted