Model studies directed toward the total synthesis of 14-membered cyclopeptide alkaloids: Synthesis of prolyl peptides via a four-component condensation

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 5, 1989, Pages 857-865

  Bowers, Margaret M ^a   Carroll, Patrick ^a   Joullié, Madeleine M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049072634     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19890000857     Document Type: Article

References (29)

1. M. Pais and F.-X. Jarreau, in 'Chemistry and Biochemistry of Amino Acids, Peptides and Proteins,' ed. B. Weinstein, Dekker, New York, 1971, vol. 1, ch. 5, p. 127
2. R. Tschesche and E. U. Kaussmann in 'The Alkaloids,' ed. R. H. Manske, Academic Press, New York, 1975, vol. 15, ch. 4, p. 165
3. U. Schmidt, A. Liebernecht, and E. Haslinger, in 'The Alkaloids,' ed. R. H. Manske, Academic Press, New York, 1985, vol. 26, ch. 6, p. 299
4. M. M. Joullie and R. F. Nutt, in 'Alkaloids: Chemical and Biological Perspectives,' ed. S. W. Pelletier, Wiley New York, 1985, vol. 3, ch. 3, p. 113
5. U. Schmidt, Pure Appl. Chem., 1986, 58, 295
6. J. R. Lewis, Nat. Prod. Rep., 1988, 3, 351.
7. R. F. Nutt and M. M. Joullie, J. Am. Chem. Soc, 1982, 104, 5852.
8. R. F. Nutt, Ph. D. Thesis, University of Pennsylvania, 1981.
9. R. F. Nutt, K. M. Chen, and M. M. Joullie, J. Org. Chem., 1984, 49, 1013.
10. M. M. Bowers-Nemia, Ph.D. Thesis, University of Pennsylvania, 1986
11. I. Ugi, Angew. Chem., Int. Ed. Engl., 1962, 1, 8.
12. Pyrrolidinol was either purchased from Aldrich Chemical Co. or synthesized as reported in M. M. Bowers-Nemia, J. Lee, and M. M. Joullie, Synth. Commun., 1983, 13, 1117.
13. O. Mitsunobu, Synthesis, 1981, 1.
14. M. J. Mintz and C. Walling, Org. Synth., 1969, 49, 9.
15. A. Failli, V. Nelson, H. Immer, and M. Gotz, Can. J. Chem., 1973,51, 2769.
16. G. Skorna and I. Ugi, Angew. Chem., Int. Ed. Engl., 1977, 16, 259.
17. G. Giesemann, E. Von Hinrichs, and I. Ugi, J. Chem. Res. S, 1982, 79.
18. I. Ugi, U. Fetzer, U. Eholzer, H. Knupfer, and K. Offermann, Newer Methods Prep. Org. Chem., 1968, 4, 37.
19. J. P. Greenstein and M. Wintz, in 'Chemistry of the Amino Acids,' Wiley, New York, 1961, vol. 2, p. 1266.
20. B. Weinstein in 'The Peptides, Chemistry and Biochemistry,' eds. B. Weinstein and S. Laude, Dekker, New York, 1970, p. 371.
21. E. W. Warnhoff, Fortschr. Chem. Org. Naturst., 1970, 18, 162.
22. Y. Ikutani, Bull Chem. Soc. Jpn., 1968, 41, 1679.
23. R. E. Bowman and H. H. Stroud, J. Chem. Soc, 1950, 1342.
24. D. M. Flanagan and M. M. Joullie, Heterocycles, 1987, 26, 2247.
25. I. Ugi, personal communication.
26. L. M. Jackman and S. Sternhell, 'Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry,' vol. 5, 2nd ed., Pergamon, New York, 1969, p. 191.
27. B. A. Frenz, 'Computing in Crystallography,' eds. H. Schenk, R. Olthof-Hazekamp, H. van Koningsveld, and G. C. Bassi, Delft University Press, 1978, 64.
28. D. T. Cromer and J. T. Waber, 'International Tables for X-ray Crystallography,' vol. 4, Table 2.2A, Kynoch Press, Birmingham, 1974.
29. J. A. Ibers and W. C. Hamilton, Acta Cryst., 1964, 17, 781.