The absolute stereochemistry of grenadamide

Tetrahedron

Volumn 60, Issue 2, 2004, Pages 341-345

  Al Dulayymi, Juma'a R ^a   Baird, Mark S ^a   Jones, Keith ^a  

^a BANGOR UNIVERSITY   (United Kingdom)

Author keywords

Grenadamide; Stereochemistry; Synthesis

Indexed keywords

3 (HEPTYLCYCLOPROPYL)PROPIONIC ACID 2 PHENYLETHANAMIDE; ALKADIENE; BUTYRIC ACID DERIVATIVE; CYCLOPROPAN 1,2 DIMETHANOL; ETHYLAMINE; GRENADAMIDE; METHANOL DERIVATIVE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; ENANTIOMER; ENZYMATIC DESYMMETRISATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0346256820     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.006     Document Type: Article

References (27)

1. Sitachitta N., Gerwick W.H. J. Nat. Prod. 61:1998;681-684.
2. He R., Deng M.-Z. Org. Lett. 4:2002;2759-2762.
3. (a) Hiyama T., Yamamoto H., Nishio K., Kitatani K., Nozaki H. Bull. Chem. Soc. Jpn. 52:1979;3632-3637.
4. (b) Wilson S.R., Prodan K.A. Tetrahedron Lett. 17:1976;4231-4234.
5. (a) Nagle D.G., Gerwick W.H. Tetrahedron Lett. 31:1990;2995-2998.
6. (b) Nagle D.G., Gerwick W.H. J. Org. Chem. 59:1994;7227-7237.
7. (c) Miyaoka H., Shigemoto T., Yamada Y. Tetrahedron Lett. 37:1996;7407-7408.
8. (d) Baba Y., Saha G., Nakao S., Iwata C., Tanaka T., Ibuka T., Ohishi H., Takemoto Y. J. Org. Chem. 66:2001;81-88.
9. (a) Critcher D.J., Connolly S., Wills M. J. Chem. Soc., Chem. Comm. 1995;139-140.
10. (b) Critcher D.J., Connolly S., Wills M. Tetrahedron Lett. 1997;3763-3766.
11. (c) Critcher D.J., Connolly S., Wills M. J. Org. Chem. 62:1997;6638-6657.
12. Seo Y., Cho K.I., Rho J.-R., Shin J. Tetrahedron. 52:1996;10583-10596.
13. (a) Buist P.H., Pon R.A. J. Org. Chem. 26:1990;6240-6241.
14. (b) Coxon G.D., Knobl S., Roberts E., Baird M.S., Al Dulayymi J.R., Besra G.S., Brennan P.J., Minnikin D.E. Tetrahedron Lett. 40:1999;6689-6692.
15. (c) Coxon G.D., Al Dulayymi J.R., Baird M.S., Knobl S., Roberts E., Minnikin D.E. Tetrahedron: Asymmetry. 14:2003;1211-1222.
16. Jiao Y., Yoshihara T., Ishikuri S., Uchino H., Ichihara A. Tetrahedron Lett. 37:1996;1039-1042.
17. Mori K., Tashiro T., Akasaka K., Ohrui H., Fattorusso E. Tetrahedron Lett. 43:2002;3719-3722.
18. (a) Kobayashi S., Tokunoh R., Shibasaki M., Shinigawa R., Murakami-Murofushi K. Tetrahedron Lett. 34:1993;4047-4050.
19. (b) Liliom K., Bittman R., Swords B., Tibor G. Mol. Pharmacol. 50:1996;616-623.
20. (a) See e.g. Jie L.K. J. Chem. Soc., Chem. Comm. 1977;78 (b) Grondin I., Smadja J., Farines M., Soulier J. Oleagineux Corps Gras Lipides. 4:1997;459-463 (c) Fenical W., Howard S.L., Paul V.J., Stallard M.O., Sun H.H. Pure Appl. Chem. 51:1979;1865-1874 (d) Shin B.A., Kim Y.R., Lee I.-S., Sung C.K., Hong J., Sim C.J., Im K.S., Jung J.H. J. Nat. Prod. 62:1999;1554-1557.
21. (a) See e.g. Jie L.K. J. Chem. Soc., Chem. Comm. 1977;78 (b) Grondin I., Smadja J., Farines M., Soulier J. Oleagineux Corps Gras Lipides. 4:1997;459-463 (c) Fenical W., Howard S.L., Paul V.J., Stallard M.O., Sun H.H. Pure Appl. Chem. 51:1979;1865-1874 (d) Shin B.A., Kim Y.R., Lee I.-S., Sung C.K., Hong J., Sim C.J., Im K.S., Jung J.H. J. Nat. Prod. 62:1999;1554-1557.
22. (a) See e.g. Jie L.K. J. Chem. Soc., Chem. Comm. 1977;78 (b) Grondin I., Smadja J., Farines M., Soulier J. Oleagineux Corps Gras Lipides. 4:1997;459-463 (c) Fenical W., Howard S.L., Paul V.J., Stallard M.O., Sun H.H. Pure Appl. Chem. 51:1979;1865-1874 (d) Shin B.A., Kim Y.R., Lee I.-S., Sung C.K., Hong J., Sim C.J., Im K.S., Jung J.H. J. Nat. Prod. 62:1999;1554-1557.
23. (a) See e.g. Jie L.K. J. Chem. Soc., Chem. Comm. 1977;78 (b) Grondin I., Smadja J., Farines M., Soulier J. Oleagineux Corps Gras Lipides. 4:1997;459-463 (c) Fenical W., Howard S.L., Paul V.J., Stallard M.O., Sun H.H. Pure Appl. Chem. 51:1979;1865-1874 (d) Shin B.A., Kim Y.R., Lee I.-S., Sung C.K., Hong J., Sim C.J., Im K.S., Jung J.H. J. Nat. Prod. 62:1999;1554-1557.
24. Grandjean D., Pale P., Chuche J. Tetrahedron. 47:1991;1215-1230.
25. Barloy-Da Silva C., Benkouider A., Pale P. Tetrahedron Lett. 41:2000;3077-3081.
26. Jorgensen M.J. J. Am. Chem. Soc. 91:1969;6430-6443.
27. 7b using the same sequence as described above.