(-)-(M,7S)-colchicine and (-)-(M,7S)-10-ethylthiocolchicide/alkyne cycloaddition reactions: Synthesis of novel colchicine derivatives by consecutive [4+2] and [3+2] cycloadditions

European Journal of Organic Chemistry

Volumn , Issue 11, 1998, Pages 2451-2460

  Brecht, René ^a   Haenel, Frank ^a   Seitz, Gunther ^a   Frenzen, Gerlinde ^b   Pilz, Astrid ^b   Guénard, Daniel ^c  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF KASSEL   (Germany)

^c INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

10 Ethylthiocolchicide, diene properties of; Atropisomerism; Colchicine; Consecutive 4+2 , 3+2 cycloadditions; Facial diastereoselectivity

Indexed keywords

EID: 0002666815     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199811)1998:11<2451::AID-EJOC2451>3.0.CO;2-3     Document Type: Article

References (24)

1. [1a] R. Brecht, F. Haenel, G. Seitz, U. Frenzen, A. Pilz, W. Massa, S. Wocadlo, Liebigs Ann. 1997, 851-857. - For recent reviews
2. [1b] H.-G. Capraro, A. Brossi in The Alkaloids (Ed.: A. Brossi), Academic Press, New York 1984, vol. 23, p. 1-70 and references therein.
3. [1c] O. Boyé, A. Brossi in The Alkaloids (Ed : A. Brossi, G. A. Cordell), Academic Press New York 1992, vol. 41, p. 125-176.
4. [2a] C. D. Campbell, C. W. Rees, J. Chem. Soc. C 1969, 742-747.
5. [2b] S. E. Whitney, M. Winters, B. Rickborn, J. Org. Chem. 1990, 55, 929-935.
6. F. M. Logullo, H. H. Seitz, L. Friedman, Org. Synth. Coll. Vol. 1973, 5, 54-59.
7. [4a] Programs used; SHELXS-86 (G. M. Sheldrick, Göttingen, 1990), SHELXS-93 (G. M. Sheldrick, Göttingen, 1993); ZORTEP (L. Zsolnay, Heidelberg, 1993).
8. [4a] Programs used; SHELXS-86 (G. M. Sheldrick, Göttingen, 1990), SHELXS-93 (G. M. Sheldrick, Göttingen, 1993); ZORTEP (L. Zsolnay, Heidelberg, 1993).
9. [4a] Programs used; SHELXS-86 (G. M. Sheldrick, Göttingen, 1990), SHELXS-93 (G. M. Sheldrick, Göttingen, 1993); ZORTEP (L. Zsolnay, Heidelberg, 1993).
10. [4b] PLATON, a multipurpose crystallographic program (A. L. Spek), Bypass: P. van der Sluis, A. L. Spek, Acta Crystallogr. A 1990, 46, 194-201.
11. [4c] Further details of the crystal structure investigations are available on request from the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen, on quoting the depository numbers CSD-408154 (for 1) and CSD-408155 (for 19), the names of the authors, and the journal citation.
12. [5a] L. velluz, G. Muller, Bull. Soc. Chim Fr. 1954, 755-758 and 1072-1075.
13. [5b] G. T. Shiau, K. K. De, R. E. Harmon, J. Pharm. Sci. 1975, 64, 646-648.
14. R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), J. Wiley, New York, 1984, pp. 149-151.
15. [7a] U. Berg, H. Bladh, M. Hoff, C. Svensson, J. Chem. Soc., Perkin Trans. 2 1997, 1697-1704.
16. [7b] E. A. Pyles, S. B. Hastie, J. Org. Chem. 1993, 58, 2751-2759.
17. [7c] Q. Shi, K. Chen, X. Chen, A. Brossi, P. Verdier-Pinard, E. Hamel, A. T. McPhail, A. Tropsha, K.-H. Lee, J. Org. Chem. 1998, 63, 4018-4025.
18. [7d] T. H. Al-Tel, M. H. Abu Zarga, S. S. Sabrie, A. J. Freyer, M. Shamma, J. Nat. Prod. 1990, 53, 623-629.
19. [7e] M. H. Abu Zarga, S. S. Sabri, T. H. Al-Tel, A.-M. Rahman, Z. Shah, M. Feroz, J. Nat. Prod. 1991, 54, 936-940.
20. [7f] R. Brecht, F. Haenel, G. Seitz, Liebigs Ann 1997, 2275-2279.
21. [7g] W. Gaffield, R. E. Lundin, R. M. Horowitz, J Chem Soc., Chem. Commun. 1984, 610-612.
22. T. Klindert, P. von Hagel, L. Baumann, G. Seitz, J. Prakt. Chem. 1997, 339, 623-632.
23. M. L. Shelanski, F. Gaskin, C. R. Cantor, Proc. Natl. Acad. Sci USA, 1973, 70, 765-768.
24. F. Zavala, D. Guénard, J. P. Robin, E. Brown, J. Med. Chem 1980, 23, 546-549.