Further studies of alkaloids from Reniera sarai: Structures of saraine-3 and isosaraine-3; absolute stereochemistry of saraine-1 and saraine-2

Tetrahedron

Volumn 52, Issue 47, 1996, Pages 14961-14974

  Guo, Yuewei ^a   Madaio, Anna ^a   Trivellone, Enrico ^a   Scognamiglio, Gennaro ^a   Cimino, Guido ^a  

^a Istituto per la Chimica di Molecole di Interesse Biologico   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ISOSARAINE 3; MACROLIDE; SARAINE 1; SARAINE 2; SARAINE 3; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SPONGE; STEREOCHEMISTRY;

RENIERA; RENIERA SARAI;

EID: 0030592794     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00908-8     Document Type: Article

References (48)

1. 1. Associated to the National Institute for the Chemistry of Biological System (CNR).
2. 2. Cimino, G.; De Stefano, S.; Scognamiglio, G.; Trivellone, E. Bull. Soc. Chim. Belg. 1986, 95, 783-800.
3. 3. Cimino, G.; Mattia, C. A.; Mazzarella, L.; Puliti, R.; Scognamiglio, G.; Spinella, A.; Trivellone, E. Tetrahedron 1989, 45, 3863-3972.
4. 4. Cimino, G.; Scognamiglio, G.; Spinella, A.; Trivellone, E. J. Nat. Prod. 1990, 53, 1519-1525.
5. 5. Cimino, G.; Spinella, A.; Trivellone, E. Tetrahedron Lett. 1989, 30, 133-136.
6. 6. Cimino, G.; Fontana, A.; Madaio, A.; Scognamiglio, G.; Trivellone, E. Magn. Reson. Chem. 1991, 29, 327-332.
7. 7. Guo, Y.-W.; Madaio, A.; Scognamiglio, G.; Trivellone, E.; Cimino, G. Tetrahedron 1996, 52, 8341-8348.
8. 8. Fusetani, N.; Yasumuro, K.; Hirota, H. Tetrahedron Lett. 1989, 30, 6891-6894.
9. 9. Nakagawa, M.; Endo, M.; Tanaka, N.; Gen-pei, L. Tetrahedron Lett. 1984, 25, 3227-3230.
10. 10. Quirion, J.-C.; Sevenet, T.; Husson, H.-P. J. Nat. Prod. 1992, 55, 1505-1508.
11. 11. Venkateswarlu, Y.; Venkata Rami Reddy, M.; Venkataswara Rao, J. J. Nat. Prod. 1994, 57, 1283-1285.
12. 12. Breakman, J. C.; Daloze, D.; Macedo de Abreu, P.; Piccini-Leopardi, C.; Germain, G.; Ven Meerssche, M. Tetrahedron Lett. 1982, 23, 4277-4281.
13. 13. Breakman, J. C.; Daloze, D.; Defay, N.; Zimmerman, D. Bull. Soc. Chim. Belg. 1984, 93, 941-944.
14. 14. Breakman, J. C.; Daloze, D.; Cimino, G.; Trivellone, E. Bull. Soc. Chim. Belg. 1988, 97, 519-524.
15. 15. Kobayashi, M.; Kawazoe, K.; Kitagawa, I. Tetrahedron Lett. 1989, 30, 4149-4152.
16. 16. Baker, B. J.; Scheuer, P. J.; Shoolery, J. N. J. Am. Chem. Soc. 1988, 110, 965-966.
17. 17. Fahy, E.; Molinski, T. F.; Harper, M. K.; Sullivan, B. W.; Faulkner, D. J. Tetrahedron Lett. 1988, 29, 3427-3428.
18. 18. Sakai, R.; Higa, T.; Jefford, C. W.; Benardinelli, G. J. J. Am. Chem. Soc. 1986, 108, 6404-6405.
19. 19. Sakai, R.; Kohmoto, S.; Higa, T.; Jefford, C. W.; Benardinelli, G. J. Tetrahedron Lett. 1987, 28, 5493-5496.
20. 20. Ichiba, T.; Sakai, R.; Kohmoto, S.; Sancy, G.; Higa, T. Tetrahedron Lett. 1988, 29, 3083-3086.
21. 21. Nakamura, H.; Deng, S.; Kobayashi, J.; Ohizumi, Y.; Tomataka, Y.; Matsuzaki, T. Tetrahedron Lett. 1987, 28, 621-624.
22. 22. Ichiba, I.; Corgiat, J. M.; Scheuer, P. J.; Borges, M. K. J. Nat. Prod. 1994, 57, 168-170.
23. 23. Tsuda, M.; Kawasaki, N.; Kobayashi, J. Tetrahedron Lett. 1994, 35, 4387-4388.
24. 24. Kobayashi, M.; Chen, Y.-J.; Aoki, S.; In, Y.; Ishida, T.; Kitagawa, I. Tetrahedron 1995, 51, 3727-3736.
25. 25. Crews, P.; Cheng, X.-C.; Adamezeski, M.; Rodriguez, J.; Jaspars, M.; Schmitz, F. J.; Traeger, S. C.; Pordesimo, E. O. Tetrahedron 1994, 50, 13567-13574.
26. 26. Tsuda, M.; Inaba, K.; Kawasaki, N.; Lionma, K.; Kobayashi, J. Tetrahedron 1996, 52, 2319-2324.
27. 27. Ohtani, I. I.; Ichiba, T.; Isoba, M.; Kelly-Borges, M.; Scheuer, P. J. J. Am. Chem. Soc. 1995, 177, 10743-10744.
28. 28. Fusetani, N.; Asai, N.; Matsunaga, S.; Honda, K.; Yasumuro, K. Tetrahedron Lett. 1994, 35, 3967-3970.
29. 29. Kong, F.; Andersen, R. J.; Allen, T. M. J. Am. Chem. Soc. 1994, 116, 6007-6008.
30. 30. Rodriguez, J. M.; Peters, B.; Kurz, L.; C. Schatzman R.; McCarley, D.; Lou, L.; Crews, P. J. Am. Chem. Soc. 1993, 115, 10436-10437.
31. 31. Rodriguez, J. M.; Crews, P. Tetrahedron Lett. 1994, 35, 4719-4722.
32. 32. Tsuda, M.; Kawasaki, N.; Kobayashi, J. Tetrahedron 1994, 50, 7957-7960.
33. 33. Kondo, K.; Shigemori, H.; Kikachi, Y.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 2480-2483.
34. 34. Kobayashi, J.; Tsuda, M.; Kawasaki, N.; Matsumoto, K.; Adachi, T. Tetrahedron Lett. 1994, 35, 4383-4386.
35. 35. M. Jaspars, M.; V. Pasupathy, V.; Crews, P. J. Org. Chem. 1994, 59, 3253-3255.
36. 36. Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron Lett. 1994, 35, 1643-1646.
37. 37. Kong, F.; Andersen, R. J. Tetrahedron 1995, 51, 2895-2906.
38. 38. Kong, F.; Andersen, R. J.; Allen, T. M. Tetrahedron 1994, 50, 6137-6144.
39. 39. Davies-Coleman, M. T.; Faulkner, D. J.; Dubowchik, G. M.; Roth, G. P.; Polson, C.; Fairchild, C. J. Org. Chem. 1993, 58, 5925-5930.
40. 40. Baldwin, J. E.; Whitehead, R. C. Tetrahedron Lett. 1992, 33, 2059-2062.
41. 41. Caprioli, V.; Cimino, G.; De Giulio, A.; Madaio, A.; Scognamiglio, G.; Trivellone, E. Comp. Biochem. Physiol. 1992, 103B, 293-296.
42. 42. Wenkert, E.; Buckwalter, B. L.; Burfitt, I. R.; Gasic, M. J.; Gottlieb, H. E.; Hagaman, E. W.; Shell, F. W. and Wakulich, P. M. Topics in Carbon-13 Spectroscopy; Levy, G. C. Ed.; John Wiley & Sons, Inc.: New York, 1976; Vol. II. pp. 84.
43. 43. Higa, T. In Studies in Natural Products Chemistry B; Atta-ur-Rahman, T. Ed.; Elsevier: Amsterdam, 1989; Vol. 5, pp. 346-353.
44. 44. Bohlman, F. Chem. Ber. 1968, 91, 2157-2162
45. 45. Haenlow, H. P.; Okuda, S.; Nakagawa, N. Tetrahedron Lett. 1964, 2553-2556.
46. 46. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4097 and references cited therein.
47. 47. Rieser, M. J.; Hui, Y.; Rupprecht, J. K.; Kozlowski, J. F.; Wood, K. V.; McLaughlin, J. L.; Hanson, P. R.; Zhuang, Z.; Hoye, R. J. Am. Chem. Soc. 1992, 114, 10203-10213.
48. 48. Scott, R. W.; Epperson, J. R.; Heathcock, C. H. J. Am. Chem. Soc. 1994, 116, 8853-8854.