Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides

Organic and Biomolecular Chemistry

Volumn 1, Issue 1, 2003, Pages 117-122

  Lizos, Dimitrios E ^a   Murphy, John A ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FREE RADICALS; IODINE COMPOUNDS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TUMORS;

ANISIDINE; ANTI-TUMOR AGENT; COERULESCINE; HORSFILINE; IODOANILINE; IODOARYL ALKENYL AZIDES; ITACONIC ACID; SPIROPYRROLIDINYLOXINDOLES; TANDEM RADICAL CYCLIZATION;

ANTIBIOTICS;

EID: 0041823428     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b208114h     Document Type: Article

References (33)

1. (a) C.-B. Cui, H. Kakeya, G. Okada, R. Onose and H. Osada, J. Antibiot., 1996, 49, 527
2. (b) C.-B. Cui, H. Kakeya and H. Osada, J. Antibiot., 1996, 49, 832
3. (c) C.-B. Cui, H. Kakeya and H. Osada, Tetrahedron, 1996, 52, 12651.
4. (a) P. R. Sebahar and R. M. Williams, J. Am. Chem. Soc., 2000, 122, 5666
5. (b) H. Wang and A. Ganesan, J. Org. Chem., 2000, 65, 4685
6. (b) L. E. Overman and M. D. Rosen, Angew. Chem., Int. Ed., 2000, 39, 4596
7. (d) T. D. Bagul, G. Lakshmaiah, T. Kawabata and K. Fuji, Org. Lett., 2002, 4, 249
8. (e) T. Lindel, Nachr. Chem., 2000, 48, 1498
9. (f) H. S. Wang and A. Ganesan, J. Org. Chem., 2000, 65, 4685
10. (g) F. von Nussbaum and S. J. Danishefsky, Angew. Chem., Int. Ed., 2000, 39, 2175.
11. S. Edmondson, S. J. Danishefsky, L. Sepp-Lorenzino and N. Rosen, J. Am. Chem. Soc., 1999, 121, 2147.
12. (a) A. Jossang, P. Jossang, H. A. Hadi, T. Sévenet and B. Bodo, J. Org. Chem., 1991, 56, 6527
13. (b) K. Jones and J. Wilkinson, J. Chem. Soc., Chem. Commun., 1992, 1767
14. (c) C. Pellegrini, C. Strässler, M. Weber and H.-J. Borschberg, Tetrahedron: Asymmetry, 1994, 5, 1979
15. (d) S.-I Bascop, J. Sapi, J.-Y. Laronze and J. Lévy, Heterocycles, 1994, 38, 725
16. (e) G. Palmisano, R. Annunziata, G. Papeo and M. Sisti, Tetrahedron: Asymmetry, 1996, 7, 1
17. (f) G. Lakshmaiah, T. Kawabata, M. Shang and K. Fuji, J. Org. Chem., 1999, 64, 1699
18. (g) C. Fischer, C. Meyers and E. M. Carreira, Helv. Chim. Acta, 2000, 83, 1175
19. (h) G. Cravotto, G. B. Giovenzana, T. Pilati, M. Sisti and G. Palmisano, J. Org. Chem., 2001, 66, 8447
20. (i) M. E. Kuehne, D. M. Roland and R. Hafter, J. Org. Chem., 1978, 43, 3705
21. (j) U. K. Syam Kumar, H. Ila and H. Junjappa, Org. Lett., 2001, 3, 4193
22. (k) M. Sonei, K. Noguchi, R. Yamagami, Y. Kawada, K. Yamada and F. Yamada, Heterocycles, 2000, 53, 7
23. (l) S. E. V. Bell, R. F. C. Brown, F. W. Eastwood and J. M. Horvath, Aust. J. Chem., 2000, 53, 183.
24. N. Anderton, P. A. Cockrum, S. M. Colegate, J. A. Edgar, K. Flower, I. Vit and R. I. Willing, Phytochemistry, 1998, 48, 437.
25. B. Patro and J. A. Murphy, Org. Lett., 2000, 2, 3599.
26. S.-Z. Zhou, S. Bommezijn and J. A. Murphy, Org. Lett., 2002, 4, 443.
27. For preliminary report, see: D. Lizos, R. Tripoli and J. A. Murphy, Chem. Commun., 2001, 2732.
28. Y. Kondo, S. Kojima and T. Sakamoto, J. Org. Chem., 1997, 62, 6507.
29. L. F. Tietze and T. Grote, Chem. Ber., 1993, 126, 2733.
30. B. R. Baker, R. E. Schaub and J. H. Williams, J. Org. Chem., 1952, 17, 116.
31. S. E. Webber, K. Okano, T. L. Little, S. H. Reich, Y. Xin, S. A. Fuhrman, D. A. Matthews, R. A. Love, T. F. Hendrickson, A. K. Patick, J. W. Meador, R. A. Ferre, E. L. Brown, C. E. Ford, S. L. Binford and S. T. Worland, J. Med. Chem., 1998, 41, 2786 note that commercial lithium borohydride was not tried in this experiment.
32. K. Jones, S. A. Brunton and R. Gosain, Tetrahedron Lett., 1999, 40, 8935.
33. A. R. Lee, W. H. Huang, T. L. Lin, K. M. Shih and H. F. Lee, J. Heterocycl. Chem., 1995, 32, 1.