Asymmetric construction of benzylic quaternary carbons from chiral malonates : Formal synthesis of both (-)- and (+)-aminoglutethimides AG and analogues

Tetrahedron Asymmetry

Volumn 7, Issue 4, 1996, Pages 1159-1166

  Fadel, Antoine ^a   Garcia Argote, Sebastien ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLUTETHIMIDE; AMINOGLUTETHIMIDE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029922501     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00122-X     Document Type: Article

References (25)

1. Martin, S.F. Tetrahedron 1980, 36, 419.
2. a) Mc Cague, R.; Rowlands, M.G. J. Med. Chem. 1992, 35, 3699.
3. b) Stanek, J.; Alder, A.; Bellus, D.; Bhatnagar, A.S.; Häusler, A.; Schieweck, K. J. Med. Chem. 1991, 34, 1329.
4. c) Foster, A.B.; Jarman, M.; Leung, C.-S.; Rowlands, M.G.; Tayol, G.N. J. Med. Chem. 1983, 26, 50.
5. a) Daly, M.J.; Jones, G.W.; Nicholls, P.J.; Smith, H.J.; Rowlands, M.G.; Bunnett, M.A. J. Med. Chem. 1986, 29, 520 and references cited therein.
6. b) Hartmann, R.W.; Batzl, C.; Pongratz, T.M.; Mannschreck, A. J. Med. Chem. 1992, 35, 2210 and references cited therein.
7. For reviews see : Harvey, H.A.; Lipton, A.; Santin, R.J. Cancer Res. (suppl.) 1982, 42, 3261.
8. Loprinzi, C.L.; Carbone, P.P. Breast Cancer in Cancer Chemotherapy and Biological Response Modifiers 9; Pinedo, H.M.; Longo, D.L.; Chabner, B.A., Eds; Elsevier: Amsterdam, New York, Oxford 1987, pp 338-357.
9. a) Thompson, E.A. Jr.; Siiteri, P.K. J. Biol. Chem. 1974, 249, 5364.
10. b) Siiteri, P.K. Cancer Res. (suppl.) 1982, 42, 3269s.
11. a) Fadel, A.; Canet, J.-L.; Salaün, J. Tetrahedron : Asymmetry 1993, 4, 27.
12. b) Canet, J.-L.; Fadel, A.; Salaün, J. J. Org. Chem. 1992, 57, 3463 and references cited therein.
13. Fadel, A.; Arzel, Ph. Tetrahedron: Asymmetry 1995, 6, 893.
14. Krapcho, A.P.; Kashdan, D.S. Tetrahedron Lett. 1975, 707.
15. Schneider, M.; Engel, N.; Boensmann, H. Angew. Chem. Int. Ed. Engl. 1984, 23, 66.
16. The absolute configuration (R)-(+)-5 was assigned comparatively to other arylmalonic ester obtained with PLE see ref. 7b, and was confirmed vide infra by comparison of the sign of glutethimide 4 with those of literature.
17. Soai, K.; Yokoyama, S.; Moshida, K. Synthesis 1987, 647.
18. Wissner, A.; Grudzinskas, C.V. J. Org. Chem. 1978, 43, 3972.
19. Mancuso, A.J.; Huang, S.L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
20. Blanchette, M.A.; Choy, W.; Davis, J.T.; Essenfeld, A.P.; Masamune, S.; Roush, W.R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
21. 20 in this solvent.
22. Fogliato, G.; Fronza, G.; Fuganti, C.; Graselli, P.; Servi, S. J. Org. Chem. 1995, 60, 5693.
23. Kukolja, S.; Grgurie, D.; Lopina. L. Croat. Chim. Acta 1961, 33, 41; U.S. patent, 2,848.455, 1958 to CIBA.
24. Scheuer, P.J.; Cohen, S.G. J. Am. Chem. Soc. 1958, 80, 4933.
25. Lepetit, S.P.A.; Patent Brit 853,954 Nov. 16.1960; C.A. 1961, 55, p 12432c.