Unusual enamide cleavage of frangufoline under mild acidic condition

Heterocycles

Volumn 43, Issue 11, 1996, Pages 2347-2351

  Suh, Dae Yeon ^a   Kim, Yong Chul ^a   Han, Yong Nam ^a   Han, Byung Hoon ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001366589     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7597     Document Type: Article

References (19)

1. Supported by a grant (G7 project, 4-4-4) from the Ministry of Science and Technology, R.O.K.
2. B. H. Han, M. H. Park, and Y. N. Han, Phytochemistry, 1990, 29, 3315; B. H. Han, M. H. Park, and J. H. Park, Pure & Appl. Chem., 1989, 61, 443.
3. B. H. Han, M. H. Park, and Y. N. Han, Phytochemistry, 1990, 29, 3315; B. H. Han, M. H. Park, and J. H. Park, Pure & Appl. Chem., 1989, 61, 443.
4. R. Tschesche and E. U. Kaußmann, The Alkaloids. Chemistry and Pharmacology, Vol. XV, ed. by R. H. F. Manske, Academic Press, New York, 1975, pp. 165-205; K. L. Bhat and M. M. Joullie, J. Chem. Ed., 1987, 64, 21. B. H. Han, M. H. Park, and Y. N. Han, Yakhak Hoeji, 1993, 37, 143.
5. R. Tschesche and E. U. Kaußmann, The Alkaloids. Chemistry and Pharmacology, Vol. XV, ed. by R. H. F. Manske, Academic Press, New York, 1975, pp. 165-205; K. L. Bhat and M. M. Joullie, J. Chem. Ed., 1987, 64, 21. B. H. Han, M. H. Park, and Y. N. Han, Yakhak Hoeji, 1993, 37, 143.
6. R. Tschesche and E. U. Kaußmann, The Alkaloids. Chemistry and Pharmacology, Vol. XV, ed. by R. H. F. Manske, Academic Press, New York, 1975, pp. 165-205; K. L. Bhat and M. M. Joullie, J. Chem. Ed., 1987, 64, 21. B. H. Han, M. H. Park, and Y. N. Han, Yakhak Hoeji, 1993, 37, 143.
7. t: 1, 12.7; 2, 9.2; 3, 17.2; 4-hydroxybenzaldehyde, 4.4 min.
8. 2Phe-CO), 193.5 (CHO).
9. 3, TMS): 5.85 (1H, s, OH), 6.96 (2H, dd, J = 1.8, 6.9 Hz), 7.82 (2H, dd, J = 1.8, 6.9 Hz), 9.88 (1H, s, CHO).
10. B. H. Han, Y. C. Kim, M. K. Park, J. H. Park, H. J. Go, H. O. Yang, D.-Y. Suh, and Y.-H. Kang, Heterocycles, 1995, 41, 1909.
11. +, 53).
12. E. Zbiral, E. L. Menard, and J. M. Muller, Holv. Chim. Acta, 1965, 48, 404; B. K. Cassels, G. Eckhardt, E. U. Kaußmann, and R. Tschesche, Tetrahedron, 1974, 30, 2461.
13. E. Zbiral, E. L. Menard, and J. M. Muller, Holv. Chim. Acta, 1965, 48, 404; B. K. Cassels, G. Eckhardt, E. U. Kaußmann, and R. Tschesche, Tetrahedron, 1974, 30, 2461.
14. 3).
15. 6: 539.2995. Found : 539.2975
16. B. H. Han and M. H. Park, Arch. Pharm. Res., 1987, 10, 203.
17. 2), 6.40 (1H, d, J = 8.1 Hz, NH-Leu), 7.06 (2H, d, J = 8.7 Hz, H-2′), 7.19-7.26 (5H, aromatic), 7.57 (1H, d, J = 8.7 Hz, NH-hyLeu), 7.80 (2H, d, J = 9.0 Hz, H-3′), 9.86 (1H, s, CHO).
18. t: 22.0 min.
19. F. K. Klein and H. Rapoport, J. Am. Chem. Soc., 1968, 90, 3576.