Synthesis of thiamacrocycles and conformational studies on their precursors

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages 343-351

  Abramovitch, Rudolph A ^a   Ye, Xiaocong ^a   Pennington, William T ^a   Schimek, George ^a   Bogdal, Dariuz ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND;

ARTICLE; CONFORMATION; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034723215     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991139z     Document Type: Article

References (32)

1. (a) Evans, D. A.; Dinsmore, C. J. Tetrahedron Lett. 1993, 43, 6038.
2. (b) Itokawa, H.; Suzuki, J.; Hitoyanagi, Y.; Kondo, K.; Takaya, K. Chem. Lett. 1993, 695.
3. (c) Yaa, X.-S.; Ehizukz, Y.; Noguchi, H.; Kinchi, F.; Shibya, M.; Itaka, Y.; Seto, H.; Sankawa, U. Chem. Pharm. Bull. 1991, 39, 2956.
4. (d) Boger, D. L.; Sakuya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204.
5. (e) Whiting, D. A.; Wood, A. F. Tetrahedron Lett. 1978, 26, 2335.
6. (f) Tius, M. A. Chem. Rev. 1988, 88, 719.
7. Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49.
8. Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614.
9. Kurihara, T.; Nakajima, Y.; Mitsunobu, O. Tetrahedron Lett. 1976, 28, 2455.
10. (a) Marshall, J. A.; DeHoff, B. S.; Crooks, S. L. Tetrahedron Lett. 1987, 28, 527.
11. (b) Marshall, J. A.; Anderson, M. W. J. Org. Chem. 1993, 58, 3912.
12. (a) Abramovitch, R. A. Unpublished results. 1993.
13. (b) Abramovitch, R. A.; Shi, Q. Heterocycles 1994, 38, 2347.
14. Roussi, G.; Zamora, E. G.; Carbonnelle, A.-C.; Beugelmans, R. Tetrahedron Lett. 1997, 38, 4405.
15. Abramovitch, R. A.; Chinnasamy, P.; Evertz, K.; Huttner, G. J. Chem. Soc., Chem. Commun. 1989, 3.
16. Abramovitch, R. A.; Boche, R. Unpublished results, 1993.
17. (a) Burley, S. K.; Petsko, G. A. Science 1985, 229, 23-28.
18. (b) Hunter, C. A. Chem. Soc. Rev. 1994, 23, 101-109.
19. (c) Kim, E.-I.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11192-11193.
20. (d) Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125.
21. (e) Adams, H.; Carver, F. J.; Hunter, C. A.; Morales, J. C.; Seward, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1542-1544.
22. (f) Wedermayer, G. H.; Patten, P. A.; Wang, L. H.; Schultz, P. A.; Stevens, R. C. Science 1997, 276, 1665.
23. (a) Rotello, V. M.; Viani, E. A.; Deslongchamps, G.; Murray, B. A.; Rebek, J. J. Am. Chem. Soc. 1993, 115, 797-798.
24. (b) Schladetzky, K. D.; Haque, T. S.; Gellman, S. H. Science 1997, 276, 1665.
25. Abramovitch, R. A.; Ye, Xiaocong. Paper presented at the 211th National Meeting of the American Chemical Society, ORGN 446, New Orleans, LA, March 1996; J. Org. Chem. 1999, 64, 5904.
26. Abramovitch, R. A.; Ye, Xiaocong. Paper presented at the 211th National Meeting of the American Chemical Society, ORGN 446, New Orleans, LA, March 1996; J. Org. Chem. 1999, 64, 5904.
27. Using PC Model from Serena Software. To ensure that a global minimum energy had been reached, the various local minimal structures were altered repeatedly until the lowest energy conformation was reached consistently. Though these computations do not take into account the influence of solvent, they do allow changes in the dielectric constant. The latter has been changed from 1.5 to 30.0 D without much change resulting in the global energy minimum conformations.
28. Wuthrich, K. J. Biol Chem. 1990, 265, 22059. Wagner, G.; Braun, W.; Havel, T. F.; Schaumann, T.; Go, N.; Wuthrich, K. J. Mol. Biol. 1987, 196, 611.
29. Wuthrich, K. J. Biol Chem. 1990, 265, 22059. Wagner, G.; Braun, W.; Havel, T. F.; Schaumann, T.; Go, N.; Wuthrich, K. J. Mol. Biol. 1987, 196, 611.
30. Jiang, X. K.; Hui, Y. Z.; Fei, Z. X. J. Chem. Soc., Chem. Commun. 1987, 689.
31. w = 0.045 for 1774 observed (I > 2σ(I)) data. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-113072 for compound 1 and CCDC-113073 for compound 2. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. (fax: (+44) 1223-336-033; e-mail deposit@ccdc.cam.ac.uk).
32. Bellamy, L. J. The Infrared Spectra of Complex Molecules; John Wiley & Sons. New York, 1958; p 64.