Structural analysis of a facile lactonization system facilitated by a "trimethyl lock"

Bioorganic Chemistry

Volumn 24, Issue 1, 1996, Pages 39-49

  Wang, Binghe ^a,b   Nicolaou, Michalis G ^a   Liu, Siming ^a,c   Borchardt, Ronald T ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b UNIVERSITY OF OKLAHOMA HEALTH SCIENCES CENTER   (United States)

^c UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE; X RAY CRYSTALLOGRAPHY;

EID: 0029892257     PISSN: 00452068     EISSN: None     Source Type: Journal    
DOI: 10.1006/bioo.1996.0005     Document Type: Article

References (29)

1. MILSTEIN, S., AND COHEN, L. A. (1972) J. Am. Chem. Soc. 94, 9158-9165.
2. MILSTEIN, S., AND COHEN, L. (1970) Proc. Nat. Acad. Sci. USA 67, 1143-1147.
3. BORCHARDT, R. T., AND COHEN, L. A. (1972) J. Am. Chem. Soc. 94, 9166-9174.
4. KING, M. M., AND COHEN, L. A. (1983) J. Am. Chem. Soc. 105, 2752-2760.
5. CASWELL, M., AND SCHMIR, G. (1980) J. Am. Chem. Soc. 102, 4815-4821.
6. AMSBERRY, K. L., AND BORCHARDT, R. T. (1991) Pharm. Res. 8, 323-330.
7. BORCHARDT, R. T., AND COHEN, L. A. (1972) J. Am. Chem. Soc. 94, 9175-9182.
8. BORCHARDT, R. T., AND COHEN, L. A. (1973) J. Am. Chem. Soc. 95, 8308-8313.
9. BORCHARDT, R. T., AND COHEN, L. A. (1973) J. Am. Chem. Soc. 95, 8313-8319.
10. BORCHARDT, R. T., AND COHEN, L. A. (1973) J. Am. Chem. Soc. 95, 8319-8326.
11. HILLERY, P. S., AND COHEN, L. A. (1983) J. Am. Chem. Soc. 105, 2760-2770.
12. HILLERY, P. S., AND COHEN, L. A. (1983) J. Org. Chem. 48, 3465-3471.
13. HILLERY, P. S., AND COHEN, L. A. (1992) Bioorganic Chem. 20, 313-322.
14. LIGHTSTONE, F. C., AND BRUICE, T. C. (1994) J. Am. Chem. Soc. 116, 10789-10790.
15. AMSBERRY, K. L., AND BORCHARDT, R. T. (1990) J. Org. Chem. 55, 5867-5877.
16. AMSBERRY, K. L., GERSTENBERGER, A. L., AND BORCHARDT, R. T. (1991) Pharm. Res. 8, 455-461.
17. UEDA, Y., MIKKILINENI, A. B., KNIP, J. O., ROSE, W. C., CASAZZA, A. M., AND VYAS, D. M. (1993) Bioorg. Med. Chem. Lett. 3, 1761-1766.
18. WANG, B., LIU, S., AND BORCHARDT, R. T. (1995) J. Org. Chem. 60, 539-543.
19. WOLFE, J. L., VANDER VELDE, D., AND BORCHARDT, R. T. (1992) J. Org. Chem. 57, 6138-6142.
20. WALKER, N. P. C., AND STUART, D. I. (1983) Acta Crystallogr. A39, 158-166.
21. BURGI, H. B., DUNITZ, J. D., LEHN, J. M., AND WIPFF, G. (1974) Tetrahedron 30, 1563-1572.
22. DUNITZ, J. D. (1979) X-Ray Analysis and the Structure of Organic Molecules, Cornell Univ. Press, Ithaca, NY.
23. KARLE, J. M., AND KARLE, I. L. (1972) J. Am. Chem. Soc. 94, 9182-9189.
24. NICOLAOU, M. G., WOLFE, J., AND BORCHARDT, R. T. J. Org. Chem. Manuscript in preparation.
25. CZARNIK, A. W. (1988) in Molecular Structure and Energetics (Liebman, J. F. and Greenberg, A., Eds.), Vol. 9, pp. 102-105, VCH, New York.
26. DANFORTH, C., NICHOLSON, A. W., JAMES, J. C., AND LOUDON, G. M. (1976) J. Am. Chem. Soc. 98, 4275-4280.
27. HERSHFIELD, R., AND SCHMIR, G. L. (1973) J. Am. Chem. Soc. 95, 8032-8040.
28. HERSHFIELD, R., AND SCHMIR, G. L. (1973) J. Am. Chem. Soc. 95, 7359-7368.
29. WINANS, R. E., AND WILCOX, C. F. (1976) J. Am. Chem. Soc. 98, 4281-4285.