Synthetic studies on asperparaline A. Synthesis of the spirosuccinimide ring system

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4519-4522

  Gonzalez, Florenci ^a   Sanz Cervera, Juan F ^a   Williams, Robert M ^a  

^a Department of Ecosystem Science and Sustainability   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPERPARALINE A; SPIROSUCCINIMIDE; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS; DRUG EFFECT; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HELMINTHIASIS;

EID: 0033546105     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00825-4     Document Type: Article

References (20)

1. 1. Hayashi, H.; Nishimoto, Y., Nozaki, H. Tetrahedron Lett. 1997, 5655-5658.
2. 2. Banks, R.M.; Blanchflower, S.E.; Everett, J.R.; Manger, B.R.; Reading, C., J. Antibiotics, 1998, 50, 840-846.
3. 3. (a) Sanz-Cervera, J.F.; Glinka, T.; Williams, R.M. J. Am. Chem. Soc. 1993, 115, 347-348;
4. (b) Sanz-Cervera, J.F.; Glinka, T.; Williams, R.M., Tetrahedron, 1993, 49, 8471-8482;
5. (c) Stocking, E.; Sanz-Cervera, J.F.; Williams, R.M.; Unkefer, C.J., J. Am. Chem. Soc. 1996, 118, 7008-7009;
6. (d) Williams, R.M.; Sanz-Cervera, J.F.; Halligan, K.; Sancenón, F., J. Am. Chem. Soc. 1998, 120, 1090-1091;
7. (e) Williams, R.M.; Sanz-Cervera, J.F.; Sancenón, F.; Marco, J.A.; Halligan, K., Bioorg. & Med. Chem. 1998, 6, 1233-1241;
8. (f) Domingo, L.R.; Sanz-Cervera, J.F.; Williams, R.M.; Picher, M.T.; Marco, J.A., J. Org. Chem. 1997, 62, 1662-1667.
9. 4. For some related 3,3-disubstituted succinimides, see: (a) Malamas, M.S.; Hohman, T.C. J. Med. Chem. 1994, 37, 2059-2070;
10. (b) Ibrahim-Ouali; M.; Sinibaldi, M-E.; Troin, Y.; Guillaume, D.; Gramain, J-C., Tetrahedron 1997, 53, 16083-16096;
11. (c) Ibrahim-Ouali; M.; Sinibaldi, M-E.; Troin, Y.; Gramain, J-C., Tetrahedron Lett. 1996, 37, 37-38;
12. (d) New, J.S.; Yevich, J.P; Eison, M.S.; Taylor, D.P.; Eison, A.S.; Riblet, L.A.; VanderMaelen, C.P.; Temple, D.L., J. Med. Chem. 1986, 29, 1476-1482;
13. (e) Nishide, K.; Katoh, T.; Imazoto, H.; Node, M., Heterocycles 1998, 47, 839-845;
14. (f) Stratford, E.S.; Curley, R.W., J. Med. Chem. 1983, 26, 1463-1469;
15. (g) Daly, M.J.; Jones, G.W.; Nicholls, P.J.; Smith, H. J.; Rowlands, M.G.; Bunnett, M.A., J. Med. Chem. 1986, 29, 520-523.
16. 5. Uno, H.; Yayama, A.; Suzuki, H. Tetrahedron 1992, 48, 8353-8368.
17. 6. Trofimov B.A. in, Heteroatomic Derivatives of Acetylene. New Polyfunctional Monomers, Reagents and Chemicals, Nauka, Moscow 1981.
18. 7. De Mayo, P.; Reid, S.T.; . Chem. Ind. (London) 1962, 1576-1577.
19. +, 224.1485; found, 224.1650.
20. 9. X-ray crystal coordinates for compound 12 will be reported elsewhere.