Intramolecular guanidine epoxide ring opening reactions

Tetrahedron Letters

Volumn 44, Issue 15, 2003, Pages 3075-3080

  Dennis, Mark ^a   Hall, Louise M ^a   Murphy, Patrick J ^a   Thornhill, Andrew J ^a   Nash, Robert ^b   Winters, Ana L ^b   Hursthouse, Michael B ^c   Light, Mark E ^c   Horton, Peter ^c  

^a BANGOR UNIVERSITY   (United Kingdom)

^b ABERYSTWYTH UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Epoxides; Guanidines; Iodocyclisations; galactosidase inhibition

Indexed keywords

EPOXIDE; GLYCOSIDASE; GUANIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; ENZYME ACTIVITY; ENZYME INHIBITION; RING OPENING; SYNTHESIS;

EID: 0037424747     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00519-7     Document Type: Article

References (32)

1. Murphy P.J., Williams H.L., Hursthouse M.B., Malik K.M.A. J. Chem. Soc., Chem. Commun. 1994;119-120.
2. Murphy P.J., Williams H.L. J. Chem. Soc., Chem. Commun. 1994;819-820.
3. Murphy P.J., Williams H.L., Hibbs D.E., Hursthouse M.B., Malik K.M.A. J. Chem. Soc., Chem. Commun. 1996;445-447.
4. Murphy P.J., Williams H.L., Hibbs D.E., Hursthouse M.B., Malik K.M.A. Tetrahedron. 52:1996;8315-8332.
5. Black G.P., Murphy P.J., Walshe N.D.A., Hibbs D.E., Hursthouse M.B., Malik K.M.A. Tetrahedron Lett. 37:1996;6943-6946.
6. Black G.P., Murphy P.J., Walshe N.D.A. Tetrahedron. 54:1998;9481-9488.
7. Black G.P., Murphy P.J., Thornhill A., Walshe N.D.A., Zanetti C. Tetrahedron. 55:1999;6547-6554.
8. Moore C.G., Murphy P.J., Williams H.L., McGown A.T., Smith N.K. Tetrahedron Lett. 44:2003;251-254.
9. For a review on other synthetic approaches to these metabolites, see: Heys L., Moore C.G., Murphy P.J. Chem. Soc. Rev. 29:2000;57-67.
10. (a) Ohtani I., Moore R.E., Runnegar M.T.C. J. Am. Chem. Soc. 114:1992;7941-7942;
11. For a review on the biological activity and synthetic approaches to cylindrospermopsin, see: Murphy, P. J.; Thomas, C. W. Chem. Soc. Rev. 2001, 30, 300-312; Heintzelman, G. R.; Fang, W. K.; Keen, S. P.; Wallace, G. A.; Weinreb, S. M. J. Am. Chem. Soc. 2002, 124, 3939-3945.
12. For a review on the biological activity and synthetic approaches to cylindrospermopsin, see: Murphy, P. J.; Thomas, C. W. Chem. Soc. Rev. 2001, 30, 300-312; 12 J. Am. Chem. Soc. 2002, 124, 3939-3945.
13. For an example using a deprotonated guanidine, see: Chen B.-C., Quinlan S.L., Reid J.G., Jass P.A., Robinson T.P., Early W.A., Delaney E.J., Humora M.J., Madding G.D., Venit J.J., Winter W.J. Tetrahedron: Asymmetry. 9:1998;1337-1340.
14. Fritsche-Lang W., Wilharm P., Hadicke E., Fritz H., Prinzbach H. Chem. Ber. 118:1985;2044-2078.
15. Le Merrer Y., Gauzy L., Gravier-Pelletier C., Depezay J.C. Bioorg. Med. Chem. 8:2000;307-320.
16. Gravier-Pelletier C., Bourissou D., Le Merrer Y., Depezay J.C. Synlett. 1996;275-277.
17. Gauzy L., Le Merrer Y., Depezay J.C. Synlett. 1998;402-404.
18. Genski T., Macdonald G., Wei X., Lewis N., Taylor R.J.K. Synlett. 1999;795-797.
19. Genski T., Macdonald G., Wei X., Lewis N., Taylor R.J.K. Arkivoc. 1:2000;266-273.
20. 2, 16 h; 73%].
21. +) requires 426.0890, found 426.0886.
22. Elliott M.C., Long M.S. Tetrahedron Lett. 43:2000;9191-9194.
23. Drake B., Patek M.L., Lebl M. Synthesis. 1994;579-581.
24. 2=0.2234.
25. Truscheit E., Frommer W., Junge B., Muller L., Schmidt D.D., Wingender W. Angew. Chem., Int. Ed. Engl. 20:1981;744-761.
26. Papandreou G., Tong M.K., Ganem B. J. Am. Chem. Soc. 115:1993;11682-11690.
27. Chan A.W.-T., Ganem B. Tetrahedron. Lett. 36:1995;811-814.
28. Fotsch C.H., Wong C.-H. Tetrahedron. Lett. 35:1994;3481-3484.
29. Knapp S., Choe Y.H., Reilly E. Tetrahedron Lett. 34:1993;4443-4446.
30. Bleriot Y., Genre-Grandpierre A., Tellier C. Tetrahedron. Lett. 35:1994;1867-1870.
31. 16.
32. Watson A.A., Nash R.J., Wormald M.R., Harvey D.J., Dealler S., Lees E., Asano N., Kizu H., Kato A., Griffiths R.C., Cairns A.J., Fleet G.W.J. Phytochemistry. 46:1997;255-259.