Stereospecific synthesis of 2-substituted bicyclic thiazolidine lactams

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1317-1320

  Subasinghe, Nalin L ^a   Khalil, Ehab M ^a   Johnson, Rodney L ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM; THIAZOLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031584913     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00067-1     Document Type: Article

References (22)

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9. 9. Baldwin, J. E.; Lee, V.; Schofield, C. J. Heterocycles, 1992, 34, 903-906.
10. 10. Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992, 114, 8778-8783.
11. 11. In one approach, we looked at condensing an aspartic acid aldehyde derivative with D-Cys(α-Me)-OMe under conditions previously shown to give the unsubstituted and 7-substituted bicyclic thiazolidine lactams. Although the intermediate epimeric thiazolidines were formed, this material did not cyclize to the desired 2-substituted bicyclic lactam upon heating.
12. 3S: C, 52.38; H, 6.59; N, 6.11 S, 13.98. Found: C, 52.54; H, 6.70; N, 6.04; S, 13.77.
13. 13. Pattenden, G.; Thom, S. M.; Jones, M. F. Tetrahedron, 1993, 49, 2131-2138.
14. 14. Seebach, D.; Boes, M.; Naef, R.; Schweizer, B. J. Am. Chem. Soc. 1983, 105, 5390-5398.
15. 15. Seebach, D.; Weber, T. Tetrahedron Lett. 1993, 24, 3315-3318.
16. 3) δ 1.12 (s, 3 H), 1.17 (s, 3 H), 1.19 (s, 3 H), 1.32 (s, 3 H), 1.89-2.15 (m, 4 H), 3.26 (d, J = 12.6 Hz, 2 H), 3.57 (d, J = 12.6 Hz, 1 H), 3.79 (s, 3 H), 3.82 (d, J = 13.8 Hz, 1 H), 3.85 (s, 3 H), 4.1 (dd, J 6.15 and 8.36 Hz, 1 H), 4.45 (dd, J = 6.6 and 8.7 Hz, 1 H), 5.14 (s, 1 H), 5.63 (s, 1 H), 7.2-7.3 (m, 10 H); FAB MS m/z 336 (MH)+.
17. 17. Compounds 6 and 7 were obtained in a diastereoisomeric ratio of 2:3 and 1:2, respectively.
18. 18. Barton, D. H. R.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1989, 30, 2619-2622.
19. 5S: C, 62.86; H, 6.59; N, 6.11. Found: C, 62.70; H, 6.49; N, 5.98.
20. 3).
21. 5S: C, 61.86; H, 6.77; N, 6.27; S, 7.18. Found: C, 61.06; H, 6.38; N, 6.31; S, 7.19.
22. 22. Atomic coordinates for the crystal structure of 14 have been deposited with the Cambridge Crystallographic Data Centre.