Total synthesis of (-)-salicylihalamide A

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1817-1820

  Snider, Barry B ^a   Song, Fengbin ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; SALICYLIHALAMIDE A;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS, HETEROCYCLIC; STEREOISOMERISM;

EID: 0035859315     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015822v     Document Type: Article

References (44)

1. Erickson, K. L.; Beutler, J. A.; Cardellina, J. H., II; Boyd, M. R. J. Org. Chem. 1997, 62, 8188-8192.
2. Erickson, K. L.; Beutler, J. A.; Cardellina, J. H., II; Boyd, M. R. J. Org. Chem. 2001, 66, 1532.
3. (a) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem., Int. Ed. 2000, 39, 4308-4310.
4. (b) Wu, Y.; Seguil, O. R.; De Brabander, J. K. Org. Lett. 2000, 2, 4241-4244. We thank Professor De Brabander for communicating this information prior to publication and for copies of the spectra of key intermediates.
5. For other syntheses, see; (a) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645-2648.
6. (b) Smith, A. B., III; Zheng, J. Synlett, in press.
7. (a) Kunze, B.; Jansen, R.; Sasse, F.; Höfle, G.; Reichenbach, H. J. Antibiot. 1998, 51, 1075-1080.
8. (b) Jansen, R.; Kunze, B.; Reichenbach, H.; Höfle, G. Eur. J. Org. Chem. 2000, 913-919.
9. (a) Galinis, D. L.; McKee, T. C.; Pannell, L. K.; Cardellina, J. H., II; Boyd, M. R. J. Org. Chem. 1997, 62, 8968-8969.
10. (b) McKee, T. C.; Galinis, D. L.; Pannell, L. K.; Cardellina, J. H., II; Laasko, J.; Ireland, C. M.; Murray, L.; Capon, R. J.; Boyd, M. R. J. Org. Chem. 1998, 63, 7805-7810.
11. (c) Suzumura, K.-i.; Takahashi, I.; Matsumoto, H.; Nagai, K.; Setiawan, B.; Rantiamodjo, R. M.; Suzuki, K.-i.; Nagano, N. Tetrahedron Lett. 1997, 38, 7573-7576.
12. Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Org. Chem. 1999, 64, 153-155.
13. Dekker, K. A.; Aiello, R. J.; Hirai, H.; Inagaki, T.; Sakakibara, T.; Suzuki, Y.; Thompson, J. F.; Yamauchi, Y.; Kojima, N. J. Antibiot. 1998, 51, 14-20.
14. For the synthesis of apicularen A, see: (a) Bhattacharjee, A.; De Brabander, J. K. Tetrahedron Lett. 2000, 41, 8069-8073.
15. (b) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217-1220.
16. (a) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215-8230.
17. (b) Fürstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731-3734.
18. Georg, G. I.; Ahn, Y. M.; Blackman, B.; Farokhi, F.; Flaherty, P. T.; Mossman, C. J.; Roy, S.; Yang, K. Chem. Commun. 2001, 255-256.
19. Feutrill, J. T.; Holloway, G. A.; Hilli, F.; Hügel, H. M.; Rizzacasa, M. A. Tetrahedron Lett. 2000, 41, 8569-8572.
20. Furber, M.; Taylor, R. J. K.; Burford, S. C. J. Chem. Soc., Perkin Trans. 1 1986, 1809-1815.
21. Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407-408.
22. (a) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 397-399.
23. (b) Raw, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2000, 41, 10357-10361.
24. (c) Approaches using amide substitution on an alkenyl iodide have also been reported: Shen, R.; Porco, J. A. Jr. Org. Lett. 2000, 2, 1333-1336.
25. Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838.
26. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511.
27. Lin, N.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9062-9072.
28. Grunwell, J. R.; Karipides, A.; Wigal, C. T.; Heinaman, S. W.; Parlow, J.; Surso, J. A.; Clayton, L.; Fleitz, F. J.; Daffner, M.; Stevens, J. E. J. Org. Chem. 1991, 56, 91-95.
29. Sato, M.; Sunami, S.; Sugita, Y.; Kaneko, C. Heterocycles 1995, 41, 1435-1444.
30. Ohmori, K.; Suzuki, T.; Miyazawa, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1993, 34, 4981-4984.
31. Sato, M.; Sunami, S.; Sugita, Y.; Kaneko, C. Chem. Pharm. Bull. 1994, 42, 839-845.
32. 24
33. (a) Mochizuki, K.; Ohmori, K.; Harumi, T.; Shizuri, Y.; Nishiyama, S.; Miyoshi, E.; Yamamura, S. Bull. Chem. Soc. Jpn. 1993, 66, 3041-3046.
34. (b) Flippin, L. A.; Brown, P. A.; Jalali-Araghi, K. J. Org. Chem. 1989, 54, 3588-3596.
35. (c) Murai, A.; Amino, Y.; Ando, T. J. Antibiot. 1985, 38, 1610-1613.
36. Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repič, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158.
37. The minor diastereomer present in the mixture is reduced to the syn diol with the opposite stereochemistry at both alcohol centers.
38. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
39. Fürstner, A.; Konetzki, I. Tetrahedron 1996, 52, 15071-15078.
40. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
41. This compound has also been prepared from 16 by a Suzuki coupling: Fürstner, A.; Seidel, G. Synlett 1998, 161-162.
42. Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. J. Org. Chem. 1994, 59, 7259-7266.
43. We thank Dr. Michael Boyd. National Cancer Institute, for arranging for the evaluation of our samples.
44. For a recent study on the biological activity, see: Boyd, M. R.; Farina, C.; Belfiore, P.; Gagliardi, S.; Kim, J. W.; Hayakawa, Y.; Beutler, J. A.; McKee, T. C.; Bowman, B. J.; Bowman, E. J. J. Pharmacol. Exp. Ther. 2001, 297, 114-120.