Total synthesis of (+)-halichlorine: An inhibitor of VCAM-1 expression

Angewandte Chemie - International Edition

Volumn 38, Issue 23, 1999, Pages 3542-3545

  Trauner, Dirk ^a   Schwarz, Jacob B ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Alkaloids; C C coupling; Natural products; Organozinc compounds; Total synthesis

Indexed keywords

ALDEHYDE; AMINOALCOHOL; CHLORINE DERIVATIVE; VASCULAR CELL ADHESION MOLECULE 1;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033521184     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I     Document Type: Article

References (41)

1. a) A. N. Barclay, M. H. Brown, S. K. A. Law, A. J. McKnighl. M. G. Tomlinson, P. A. Van der Merwe, The Leucocyte Antigen Facts Book, Academic Press, Oxford, 1997;
2. b) C. A. Foster, J. Allergy Clin. Immunol. 1996, S272;
3. c) T. A. Springer, Cell 1994, 76, 301:
4. d) T. M. Carlos, J. K. Harlan. Blood 1994, 84, 2068.
5. a) M. Kuramoto, C. Tong, K. Yamada, T. Chiba, Y. Hayashi, D. Uemura, Tetrahedron Lett. 1996, 37, 3867;
6. b) H. Arimoto, I. Hayakawa, M. Kuramoto, D. Uemura, Tetrahedron Lett. 1998, 39, 861.
7. T. Chou, M. Kuramoto, Y. Onati, K. Yamada, M. Shikano, K. Yazawa, D. Uemura, Tetrahedron Lett. 1996, 37, 3871.
8. Synthetic approaches to halichlorine and pinnaic acid: a) S. P. Keen, S. M. Weinreb, J. Org. Chem. 1998, 63, 6739; b) H. Arimoto, S. Asano, D. Uemura, Tetrahedron Lett. 1999, 40. 3583; S. Lee, Z. Zhao. Org. Lett. 1999. 1, 681.
9. Synthetic approaches to halichlorine and pinnaic acid: a) S. P. Keen, S. M. Weinreb, J. Org. Chem. 1998, 63, 6739; b) H. Arimoto, S. Asano, D. Uemura, Tetrahedron Lett. 1999, 40. 3583; S. Lee, Z. Zhao. Org. Lett. 1999. 1, 681.
10. Synthetic approaches to halichlorine and pinnaic acid: a) S. P. Keen, S. M. Weinreb, J. Org. Chem. 1998, 63, 6739; b) H. Arimoto, S. Asano, D. Uemura, Tetrahedron Lett. 1999, 40. 3583; S. Lee, Z. Zhao. Org. Lett. 1999. 1, 681.
11. D. Trauner, S. J. Danishefsky, Tetrahedron Lett. 1999, 40, 6513.
12. a) J. A. Ragan, M. C Claffey, Heterocycles 1995, 41, 57:
13. b) M. D. Ennis, R. L. Hoffman, N. B. Ghazal, D. W. Old, P. A. Mooney, J. Org. Chem. 1996, 61, 5813;
14. for comprehensive reviews on the chemistry of bicyclic lactams. see c) A. I. Meyers, G. P. Brengel, Chem. Commun. 1997, 1;
15. d) D. Romo, A. I. Meyers. Tetrahedron 1991, 47, 9503.
16. 3 Suzuki couplings, see b) A. Balog, C. Harris, K. Savin, K.-G. Zhang, T-C. Chou, S. J. Danishefsky, Angew. Chem. 1998. 110, 2821; Angew. Chem. Int. Ed. 1998, 37, 2675; c) B. M. Trost, C. B. Lee, J. Am. Chem. Soc: 1998, 120, 6818; d) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana. Tetrahedron Lett. 1998, 39, 4027; e) A. Fürstner, I. Konetzki, J. Org. Chem. 1998, 63, 3072; f) M. Ohba, N. Kawase, T. Fujii. J. Am. Chem. Soc. 1996, 118, 8250; g) C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014.
17. 3 Suzuki couplings, see b) A. Balog, C. Harris, K. Savin, K.-G. Zhang, T-C. Chou, S. J. Danishefsky, Angew. Chem. 1998. 110, 2821; Angew. Chem. Int. Ed. 1998, 37, 2675; c) B. M. Trost, C. B. Lee, J. Am. Chem. Soc: 1998, 120, 6818; d) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana. Tetrahedron Lett. 1998, 39, 4027; e) A. Fürstner, I. Konetzki, J. Org. Chem. 1998, 63, 3072; f) M. Ohba, N. Kawase, T. Fujii. J. Am. Chem. Soc. 1996, 118, 8250; g) C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014.
18. 3 Suzuki couplings, see b) A. Balog, C. Harris, K. Savin, K.-G. Zhang, T-C. Chou, S. J. Danishefsky, Angew. Chem. 1998. 110, 2821; Angew. Chem. Int. Ed. 1998, 37, 2675; c) B. M. Trost, C. B. Lee, J. Am. Chem. Soc: 1998, 120, 6818; d) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana. Tetrahedron Lett. 1998, 39, 4027; e) A. Fürstner, I. Konetzki, J. Org. Chem. 1998, 63, 3072; f) M. Ohba, N. Kawase, T. Fujii. J. Am. Chem. Soc. 1996, 118, 8250; g) C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014.
19. 3 Suzuki couplings, see b) A. Balog, C. Harris, K. Savin, K.-G. Zhang, T-C. Chou, S. J. Danishefsky, Angew. Chem. 1998. 110, 2821; Angew. Chem. Int. Ed. 1998, 37, 2675; c) B. M. Trost, C. B. Lee, J. Am. Chem. Soc: 1998, 120, 6818; d) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana. Tetrahedron Lett. 1998, 39, 4027; e) A. Fürstner, I. Konetzki, J. Org. Chem. 1998, 63, 3072; f) M. Ohba, N. Kawase, T. Fujii. J. Am. Chem. Soc. 1996, 118, 8250; g) C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014.
20. 3 Suzuki couplings, see b) A. Balog, C. Harris, K. Savin, K.-G. Zhang, T-C. Chou, S. J. Danishefsky, Angew. Chem. 1998. 110, 2821; Angew. Chem. Int. Ed. 1998, 37, 2675; c) B. M. Trost, C. B. Lee, J. Am. Chem. Soc: 1998, 120, 6818; d) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana. Tetrahedron Lett. 1998, 39, 4027; e) A. Fürstner, I. Konetzki, J. Org. Chem. 1998, 63, 3072; f) M. Ohba, N. Kawase, T. Fujii. J. Am. Chem. Soc. 1996, 118, 8250; g) C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014.
21. 3 Suzuki couplings, see b) A. Balog, C. Harris, K. Savin, K.-G. Zhang, T-C. Chou, S. J. Danishefsky, Angew. Chem. 1998. 110, 2821; Angew. Chem. Int. Ed. 1998, 37, 2675; c) B. M. Trost, C. B. Lee, J. Am. Chem. Soc: 1998, 120, 6818; d) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana. Tetrahedron Lett. 1998, 39, 4027; e) A. Fürstner, I. Konetzki, J. Org. Chem. 1998, 63, 3072; f) M. Ohba, N. Kawase, T. Fujii. J. Am. Chem. Soc. 1996, 118, 8250; g) C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014.
22. 3 Suzuki couplings, see b) A. Balog, C. Harris, K. Savin, K.-G. Zhang, T-C. Chou, S. J. Danishefsky, Angew. Chem. 1998. 110, 2821; Angew. Chem. Int. Ed. 1998, 37, 2675; c) B. M. Trost, C. B. Lee, J. Am. Chem. Soc: 1998, 120, 6818; d) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana. Tetrahedron Lett. 1998, 39, 4027; e) A. Fürstner, I. Konetzki, J. Org. Chem. 1998, 63, 3072; f) M. Ohba, N. Kawase, T. Fujii. J. Am. Chem. Soc. 1996, 118, 8250; g) C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014.
23. 3 Suzuki couplings, see b) A. Balog, C. Harris, K. Savin, K.-G. Zhang, T-C. Chou, S. J. Danishefsky, Angew. Chem. 1998. 110, 2821; Angew. Chem. Int. Ed. 1998, 37, 2675; c) B. M. Trost, C. B. Lee, J. Am. Chem. Soc: 1998, 120, 6818; d) M. Sasaki, H. Fuwa, M. Inoue, K. Tachibana. Tetrahedron Lett. 1998, 39, 4027; e) A. Fürstner, I. Konetzki, J. Org. Chem. 1998, 63, 3072; f) M. Ohba, N. Kawase, T. Fujii. J. Am. Chem. Soc. 1996, 118, 8250; g) C. R. Johnson, M. P. Braun, J. Am. Chem. Soc. 1993, 115, 11014.
24. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
25. For a phosphonate representing the C15-C21 portion of halichlorine, see Ref. [4a].
26. a) J. C. Gilbert, U. Weerasooriya, J. Org. Chem. 1979, 44, 4997;
27. b) M. Rao, M. A. McGuigan, X. Zhang, Z. Shaked, W. A. Kinney, M. Bulliard, B. Laboue, N. E. Lee, J. Org. Chem. 1997, 62, 4541;
28. c) D. T. Hung, J. B. Nerenberg, S. L. Schreiber, J. Am. Chem. Soc. 1996, 118, 11054.
29. a) P. Wipf, S. Ribe, J. Org. Chem. 1998, 63, 6454;
30. b) P. Wipf, P. D. G. Coish, Tetrahedron Lett. 1997, 38, 5073;
31. c) P. Wipf, W. Xu, Tetrahedron Lett. 1994, 35, 5197.
32. a) K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833;
33. b) K. Soai, K. Takahashi, J. Chem. Soc: Perkin Trans. 1 1994, 1257:
34. c) C. Dreisbach, G. Wischnewski, U. Kragl, C. Wandrey, J. Chem. Soc. Perkin Trans. 1 1995, 875.
35. a) D. Meng, P. Bertinato, A. Balog, D.-S. Su, T. Kamenecka, E. J. Sorensen, S. J. Danishefsky, J. Am. Chem. Soc. 1997, 119, 10073;
36. b) A. B. Jones, A. Villalobos, R. G. Linde, S. J. Danishefsky, J. Org. Chem. 1990, 55, 2786.
37. a) W. Zhang, M. J. Robins, Tetrahedron Lett. 1992, 33, 1177:
38. b) J. D. White, J. C-. Amedio, S. Gut, S. Ohira, L. R. Jayasinghe, J. Org. Chem. 1992, 57, 2270.
39. a) E. P. Boden, G. E. Keck, J. Org. Chem. 1985, 50, 2394;
40. b) A. E. Weber, M. G. Steiner, P. A. Krieter, A. E. Coletti, J. R. Tata, T. A. Halgren, R. G. Ball, J. J. Doyle, T. W. Schorn, R. A. Stearns, R. R. Miller, P. K. S. Siegl, W. J. Greenlee, A. A. Patchett, J. Med. Chem. 1992, 35, 3755.
41. We thank Professor D. Uemura and Dr. H. Arimoto for kindly providing us with halichlorine and its associated spectra as well as spectra of its methanolysis product.