Practical and stereoselective synthesis of a pentacyclic guanidine system: Synthetic studies toward ptilomycalin A and related compounds

Tetrahedron

Volumn 56, Issue 2, 2000, Pages 187-192

  Nagasawa, Kazuo ^a   Georgieva, Angelina ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

1,3 dipolar cycloaddition reaction; Cyclic guanidines; Nitrones; Ptilomycalin A

Indexed keywords

GUANIDINE DERIVATIVE; PTILOMYCALIN A; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0034614331     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01005-4     Document Type: Article

References (44)

1. (a) Riordan, J. F. Mol. Cell. Biochem. 1979, 26, 71.
2. (b) Hart, K. W.; Clarke, A. R.; Wigley, D. B.; Waldman, A. D. B.; Chia, W. N.; Barstow, D. A.; Atkinson, T.; Jones, J. B.; Holbrook, J. J. Biochem. Biophys. Acta 1987, 914, 294.
3. (a) Fink, M. L.; Bodanszky, M. J. Am. Chem. Soc. 1976, 98, 974.
4. (b) Dietrich, B.; Fyles, T. M.; Lehn, J. M.; Pease, L. G.; Fyles, D. L. J. Chem. Soc., Chem. Commun. 1978, 934.
5. (c) Cotton, F. A.; Day, V. W.; Hazen, Jr. E. E.; Larsen, S. J. Am. Chem. Soc. 1973, 95, 4834.
6. (a) Alcazar, V.; Moran, J. R.; de Mendoza, J. Tetrahedron Lett. 1995, 36, 3941.
7. (b) Howard-Jones, A.; Murphy, P. J.; Thomas, D. A. J. Org. Chem. 1999, 64, 1039.
8. (c) Chinchilla, R.; Najera, C.; Sanchez-Agullo, P. Tetrahedron: Asymmetry 1994, 5, 1393.
9. (d) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910.
10. (e) Isobe, T.; Fukuda, K.; Ishikawa, T. Tetrahedron: Asymmetry 1998, 9, 1729.
11. Schmidtchen F.P., Berger M. Chem. Rev. 97:1997;1609. and references therein.
12. For reviews see: Berlinck, R. G. S. Nat. Prod. Rep. 1999, 16, 339; 1996, 13, 377.
13. For reviews see: Berlinck, R. G. S. Nat. Prod. Rep. 1999, 16, 339; 1996, 13, 377.
14. (a) Kashman, Y.; Hirsh, S.; McConnell, O. J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. J. Am. Chem. Soc. 1989, 111, 8925.
15. (b) Ohtani, I.; Kusumi, T.; Kakisawa, H.; Kashman, Y.; Hirsh, S. J. Am. Chem. Soc. 1992, 114, 8472.
16. (c) Ohtani, I.; Kusumi, T.; Kakisawa, H. Tetrahedron Lett. 1992, 33, 2525.
17. (a) Jares-Erijman, E. A.; Ingrum, A. L.; Carney, J. R.; Rinehart, K. L.; Sakai, R. J. Org. Chem. 1993, 58, 4805.
18. (b) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, I.; Riccio, R.; Ferri, S.; Spampinato, S.; Speroni, E. J. Nat. Prod. 1993, 56, 1007.
19. Snider, B. B.; Shi, Z. J. Org. Chem. 1992, 57, 2526; Tetrahedron Lett. 1993, 34, 2099; J. Org. Chem. 1993, 58, 3828; J. Am. Chem. Soc. 1994, 116, 549.
20. Snider, B. B.; Shi, Z. J. Org. Chem. 1992, 57, 2526; Tetrahedron Lett. 1993, 34, 2099; J. Org. Chem. 1993, 58, 3828; J. Am. Chem. Soc. 1994, 116, 549.
21. Snider, B. B.; Shi, Z. J. Org. Chem. 1992, 57, 2526; Tetrahedron Lett. 1993, 34, 2099; J. Org. Chem. 1993, 58, 3828; J. Am. Chem. Soc. 1994, 116, 549.
22. Snider, B. B.; Shi, Z. J. Org. Chem. 1992, 57, 2526; Tetrahedron Lett. 1993, 34, 2099; J. Org. Chem. 1993, 58, 3828; J. Am. Chem. Soc. 1994, 116, 549.
23. (a) Murphy, P. J.; Williams, H. L.; Hursthouse, M. B.; Abdul Malik, K. M. J. Chem. Soc., Chem. Commun. 1994, 119.
24. (b) Murphy, P. J.; Williams, H. L. J. Chem. Soc., Chem. Commun. 1994, 819.
25. (c) Murphy, P. J.; Williams, H. L.; Hibbs, D. E.; Hursthouse, M. B.; Abdul Malik, K. M. Tetrahedron 1996, 52, 8315.
26. Overman L.E., Rabinowitz M.H., Renhowe P.A. J. Am. Chem. Soc. 117:1995;2657.
27. Coffey D.S., McDonald A.I., Overman L.E., Stappenbeck F. J. Am. Chem. Soc. 121:1999;6944.
28. Murahashi S., Shiota T. Tetrahedron Lett. 28:1987;2383.
29. For reviews see: (a) Tufairello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984.
30. (b) Special issue, Tetrahedron, 1985, 41, No. 17, 3447-3568.
31. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1.
32. (d) Frederickson, M. Tetrahedron 1997, 53, 403.
33. (e) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
34. LeBel N.A., Spurlock L.A. J. Org. Chem. 29:1964;1337.
35. (a) Tufariello, J. J.; Mullen, G. B.; Tegeler, J. J.; Trybulski, E. J.; Wong, S. C.; Ali, Sk. A. J. Am. Chem. Soc. 1979, 101, 2435.
36. (b) Tufariello, J. J.; Puglis, J. M. Tetrahedron Lett. 1986, 27, 1489.
37. (a) Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677.
38. (b) Iwanowicz, E. J.; Poss, M. A.; Lin, J. Syn. Comm. 1993, 23, 1443.
39. Ley S.V., Norman J., Griffith W.P., Marsden S.P. Synthesis. 1994;639.
40. (a) Ali, Sk. A.; Wazeer, M. I. M. Tetrahedron Lett. 1993, 34, 137.
41. (b) Ali, Sk. A.; Wazeer, M. I. M. Tetrahedron 1993, 49, 4339.
42. 3) δ 147.62, 80.06, 61.78, 52.08, 39.20, 34.10, 29.81, 24.69, 17.56.
43. Cicchi S., Hold I., Brandi A. J. Org. Chem. 58:1993;5274.
44. w=0.065.