A caveat in the application of the exciton chirality method to N,N- dialkyl amides. Synthesis and structural revision of AT2433-B1 [12]

Journal of the American Chemical Society

Volumn 121, Issue 15, 1999, Pages 3801-3802

  Chisholm, John D ^a   Golik, Jerzy ^b   Krishnan, Bala ^b   Matson, James A ^b   Van Vranken, David L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE;

ANALYTIC METHOD; ANISOTROPY; CIRCULAR DICHROISM; DRUG SYNTHESIS; GLYCOSYLATION; LETTER; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033594499     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9842924     Document Type: Letter

References (22)

1. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry; University Science Books: New York, 1983.
2. Nakanishi, K.; Berova, N. In Circular Dichroism: Principles and Applications; Nakanishi, K., Berova, N., Woody, R. W., Eds.; VCH: New York, 1994; p 361.
3. Polonski, T. J. Org. Chem. 1993, 58, 258.
4. Golik, J.; Doyle, T. W.; Krishnan, B.; Dubay, G.; Matson, J. A. J. Antibiot. 1989, 42, 1784.
5. Matson, J. A.; Claridge, C.; Bush, J. A.; Titus, J.; Bradner, W. T.; Doyle, T. W.; Horan, A. C.; Patel, M. J. Antibiot. 1989, 42, 1547.
6. Bergman, J.; Koch, E.; Pelcman, B. Tetrahedron Lett. 1995, 36, 3945.
7. Gribble, G. W.; Berthel, S. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers: Dodrecht, 1993; Vol. 12.
8. Chisholm, J. D.; Van Vranken, D. L. J. Org. Chem. 1995, 60, 6672.
9. Gilbert, E. J.; Van Vranken, D. L. J. Am. Chem. Soc. 1996, 118, 5500.
10. Gilbert, E. J.; Ziller, J. W.; Van Vranken, D. L. Tetrahedron 1997, 53, 16553.
11. Anizon, F.; Belin, L.; Moreau, P.; Sancelme, M.; Voldoire, A.; Prudhomme, M.; Ollier, M.; Severe, D.; Riou, J. F.; Bailly, C.; Fabbro, D.; Meyer, T. J. Med. Chem. 1997, 40, 3456.
12. Ohkubo, M.; Kawamoto, H.; Ohno, T.; Nakano, M.; Morishima, H. Tetrahedron 1997, 53, 585.
13. Steglich, W. Pure Appl. Chem. 1989, 61, 281.
14. Joyce, R. P.; Gainor, J. A.; Weinreb, S. M. J. Org. Chem. 1987, 52, 1177.
15. Samuelsson, B.; Johansson, R. J. Chem. Soc., Perkin Trans. I 1984, 2371.
16. Roush, W. R.; Hunt, J. A. J. Org. Chem. 1995, 60, 798.
17. Groneberg, R. D.; Miyazaki, T.; Stylianides, N. A.; Schulze, T. J.; Stahl, W.; Schreiner, E. P.; Suzuki, T.; Iwabuchi, Y.; Smith, A. L.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7593.
18. Lee, M. D.; Dunne, T. S.; Chang, C. C.; Ellestad, G. A.; Siegel, M. M.; Morton, G. O.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466.
19. Golik, J.; Clardy, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. J. Am. Chem. Soc. 1987, 109, 3461.
20. Kawai, M.; Nagai, U.; Katsumi, M. Tetrahedron Lett. 1975, 16, 3165.
21. 2O) predict this conformation to be unfavorable relative to E and Z amide conformations shown in Scheme 6.
22. Lo, L. C.; Berova, N.; Nakanishi, K.; Morales, E. Q.; Vazquez, J. T. Tetrahedron Asymm. 1993, 4, 321.