The guanidine metabolites of Ptilocaulis spiculifer and related compounds; isolation and synthesis

Chemical Society Reviews

Volumn 29, Issue 1, 2000, Pages 57-67

  Heys, Laura ^a   Moore, Christopher G ^a   Murphy, Patrick J ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034400884     PISSN: 03060012     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903712h     Document Type: Article

References (43)

1. For leading references see: R. G. S. Berlinck, Nat. Prod. Rep., 1995, 377.
2. (a) Y. Kashman, S. Hirsh, O. J. McConnell, I. Ohtani, T. Kusumi and H. J. Kakisawa, J. Am. Chem. Soc., 1989, 111, 8925;
3. (b) I. Ohtani, T. Kusumi, H. Kakisawa, Y. Kashman and S. Hirsh, J. Am. Chem. Soc., 1992, 114, 8472.
4. R. G. S. Berlinck, J. C. Braekman, D. Daloze, K. Hallenga, R. Ottinger, I. Bruno and R. Riccio, Tetrahedron Lett., 1990, 31, 6531.
5. A. D. Patil, N. V. Kumar, W. C. Kokke, M. F. Bean, A. J. Freyer, C. De Brosse, S. Mai, A. Truneh, D. J. Faulkner, B. Carte, A. L. Breen, R. P. Hertzberg, R. K. Johnson, J. W. Westley and B. C. M. Potts, J. Org. Chem., 1995, 60, 1182.
6. E. Palagiano, S. De Marino, L. Minale, R. Riccio, F. Zollo, M. Iorizzi, J. B. Carré, C. Debitus, L. Lucarain and J. Provost, Tetrahedron, 1995, 51, 3675.
7. G. C. Harbour, A. A. Tymiak, K. L. Rinehart, P. D. Shaw, R. G. Hughes, S. A. Mizsak, J. H. Coats, G. E. Zurenko, L. H. Li and S. L. Kuentzel, J. Am. Chem. Soc., 1981, 103, 5604.
8. E. A. Jares-Erijman, R. Sakai and K. L. Rinehart, J. Org. Chem., 1991, 56, 5712.
9. R. Tavares, D. Daloze, J. C. Braekman, E. Hadju, G. Muricy and R. W. M. van Soest, Biochem. Syst. Ecol., 1994, 22, 645.
10. R. G. S. Berlinck, J. C. Braekman, D. Daloze, I. Bruno, R. Riccio, S. Ferri, S. Spampinato and E. Speroni, J. Nat. Prod., 1993, 56, 1007.
11. E. A. Jares-Erijman, A. L. Ingrum, J. R. Carney, K. L. Rinehart and R. Sakai, J. Org. Chem., 1993, 58, 4805.
12. (a) R. G. S. Berlinck, J. C. Braekman, D. Daloze, I. Bruno, R. Riccio, D. Rogeau and P. Amade, J. Nat. Prod., 1992, 55, 528;
13. (b) E. A. Jares-Erijman, A. A. Ingrum, F. Sun and K. L. Rinehart, J. Nat. Prod., 1993, 56, 2186.
14. 4
15. (a) B. B. Snider, J. Chen, A. D. Patil and A. J. Freyer, Tetrahedron Lett., 1996, 37, 6977;
16. (b) the alkene stereochemistry in batzelladine E has also been recently reassigned, see, B. B. Snider and J. Chen, Tetrahedron Lett., 1998, 39, 5697;
17. (c) the absolute stereochemistry of batzelladine B has been determined by synthesis of a degradation product and is as shown in the scheme, however this is the opposite of the arbitrary stereochemistry chosen by the authors of reference 4; A. S. Franklin, S. K. Ly, G. H. Mackin, L. E. Overman and A. J. Shaka, J. Org. Chem., 1999, 64, 1512.
18. A. D. Patil, A. J. Freyer, P. B. Taylor, B. Carté, G. Zuber, R. K. Johnson and D. J. Faulkner, J. Org. Chem, 1997, 62, 1814.
19. (a) G. P. Black, P. J. Murphy and N. D. A. Walshe, Tetrahedron, 1998, 54, 9481;
20. (b) G. P. Black, P. J. Murphy, A. Thornhill, N. D. A. Walshe and C. Zanetti, Tetrahedron, 1999, 55, 6547.
21. B. B. Snider and W. C. Faith, J. Am. Chem. Soc., 1984, 106, 1443.
22. (a) B. B. Snider and Z. Shi, J. Org. Chem., 1992, 57, 2526;
23. (b) B. B. Snider and Z. Shi, J. Org. Chem., 1993, 58, 3828.
24. B. B. Snider and Z. Shi, Tetrahedron Lett., 1993, 34, 2099.
25. B. B. Snider and Z. Shi, J. Am. Chem. Soc., 1994, 116, 549.
26. L. E. Overman and M. H. Rabinowitz, J. Org. Chem., 1993, 58, 3235.
27. L. E. Overman, M. H. Rabinowitz and P. A. Renhowe, J. Am. Chem. Soc., 1995, 117, 2657.
28. A. I. McDonald and L. E. Overman, J. Org. Chem., 1999, 64, 1520.
29. (a) P. J. Murphy, H. L. Williams, M. B. Hursthouse and K. M. A. Malik, J. Chem. Soc., Chem. Commun., 1994, 119;
30. (b) P. J. Murphy and H. L. Williams, J. Chem. Soc., Chem. Commun., 1994, 819;
31. (c) P. J. Murphy, H. L. Williams, D. E. Hibbs, M. B. Hursthouse and K. M. A. Malik, Tetrahedron, 1996, 52, 8315.
32. G. P. Black, P. J. Murphy, N. D. A. Walshe, D. E. Hibbs, M. B. Hursthouse and K. M. A. Malik, Tetrahedron Lett., 1996, 37, 6943.
33. 13c
34. S. Louwrier, M. Ostendorf, A. Tuynman and H. Hiemstra, Tetrahedron Lett., 1996, 37, 905.
35. (a) S. Louwrier, M. Ostendorf, A. Boom, H. Hiemstra and W. N. Speckamp, Tetrahedron, 1996, 52, 2603;
36. (b) S. Louwrier, A. Tuynman and H. Hiemstra, Tetrahedron, 1996, 52, 2629.
37. A. V. Rama Rao, M. K. Gurjar and J. Vasudevan, J. Chem. Soc., Chem. Commun., 1995, 1369.
38. C. L. Hannon and E. V. Anslyn, Bioorg. Chem. Front., 1993, 3, 193.
39. For leading references see: F. P. Schmidtchen and M. Berger, Chem. Rev., 1997, 97, 1609.
40. I. Ohtani, T. Kusumi and H. Kakisawa, Tetrahedron Let., 1992, 33, 2525.
41. P. J. Murphy, H. L. Williams, D. E. Hibbs, M. B. Hursthouse and K. M. A. Malik, Chem. Commun., 1996, 445.
42. (a) A.-L. Grillot and D. J. Hart, Tetrahedron, 1995, 51, 11377;
43. (b) A.-L. Grillot and D. J. Hart, Heterocycles, 1994, 39, 435.