Asymmetric total synthesis of (-)-cribrostatin 4 (renieramycin H)

Angewandte Chemie - International Edition

Volumn 46, Issue 9, 2007, Pages 1517-1520

  Vincent, Guillaume ^a,b   Williams, Robert M ^a,b  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b UNIVERSITY OF COLORADO CANCER CENTER   (United States)

Author keywords

Antitumor agents; Heterocycles; Natural products; Pictet Spengler reaction; Total synthesis

Indexed keywords

CYCLIZATION; ONCOLOGY; ORGANIC COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ANTITUMOR AGENTS; HETEROCYCLES; NATURAL PRODUCTS; PICTET-SPENGLER REACTION; TOTAL SYNTHESIS;

ANTIBIOTICS;

CRIBROSTATIN 4; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; PH; STEREOISOMERISM; SYNTHESIS;

HYDROGEN-ION CONCENTRATION; ISOQUINOLINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 34247264233     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604126     Document Type: Article

References (38)

1. For a review, see: J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669-1730.
2. G. J. Aune, T. Furuta, Y. Pommier, Anti-Cancer Drugs 2002, 13, 545-555.
3. M. E. Flanagan, R. M. Williams, J. Org. Chem. 1995, 60, 6791-6797.
4. a) J. D. Scott, R. M. Williams, Angew. Chem. 2001, 113, 1511-1513;
5. Angew. Chem. Int. Ed. 2001, 40, 1463-1465;
6. b) J. D. Scott, R. M. Williams, J. Am. Chem. Soc. 2002, 124, 2951-2956.
7. a) J. W. Lane, Y. Chen, R. M. Williams, J. Am. Chem. Soc. 2005, 127, 12684-12690;
8. b) J. W. Lane, A. Estevez, K. Mortara, O. Callan, J. R. Spencer, R. M. Williams, Bioorg. Med. Chem. Lett. 2006, 16, 3180-3183.
9. a) R. M. Williams, T. Glinka, R. Gallegos, P. P. Ehrlich, M. E. Flanagan, H. Coffman, G. Park, Tetrahedron 1991, 47, 2629-2642;
10. b) M. E. Flanagan, S. B. Rollins, R. M. Williams, Chem. Biol. 1995, 2, 147-156;
11. c) B. Herberich, J. D. Scott, R. M. Williams, Bioorg. Med. Chem. 2000, 8, 523-532.
12. D. Fishlock, R. M. Williams, Org. Lett. 2006, 8, 3299-3301.
13. a) R. M. Williams, T. Glinka, M. E. Flanagan, R. Gallegos, H. Coffman, D. Pei, J. Am. Chem. Soc. 1992, 114, 733-740;
14. b) R. M. Williams, M. E. Flanagan, T. N. Tippie, Biochemistry 1994, 33, 4086-4092;
15. c) R. M. Williams, B. Herberich, J. Am. Chem. Soc. 1998, 120, 10272-10273.
16. P. S. Parameswaran, G. C. Naik, S. Y. Kamat, B. N. Pramanik, Indian J. Chem. Sect. B 1998, 37, 1258-1263.
17. N. Saito, H. Sakai, K. Suwanborirux, S. Pummangura, A. Kubo, Heterocycles 2001, 55, 21-28.
18. G. R. Pettit, J. C. Knight, J. C. Collins, D. L. Herald, R. K. Pettit, M. R. Boyd, V. G. Young, J. Nat. Prod. 2000, 63, 793-798.
19. C. Chan, R. Heid, S. Zheng, J. Guo, B. Zhou, T. Furuuchi, S. J. Danishefsky, J. Am. Chem. Soc. 2005, 127, 4596-4598.
20. W. Jin, S. Metobo, R. M. Williams, Org. Lett. 2003, 5, 2095-2098.
21. D. A. Evans, E. B. Sjogren, Tetrahedron Lett. 1985, 26, 3783-3786.
22. B. Herberich, M. Kinugawa, A. Vazquez, R. M. Williams, Tetrahedron Lett. 2001, 42, 543-546.
23. a) W. Jin, R. M. Williams, Tetrahedron Lett. 2003, 44, 4635-4639;
24. b) R. M. Williams, M.-N. Im, Tetrahedron Lett. 1988, 29, 6075-6078;
25. c) R. M. Williams, M.-N. Im, J. Am. Chem. Soc. 1991, 113, 9276-9286;
26. d) R. M. Williams, Aldrichimica Acta 1992, 25, 11-25;
27. e) D. M. Bender, Williams, R.M. J. Org. Chem. 1997, 62, 6690-6691;
28. f) K. A. Dastlik, U. Sundermeier, D. M. Johns, Y. Chen, R. M. Williams, Synlett 2005, 693-696.
29. 2); see, for example: a) Y. Chen, PhD thesis, Colorado State University (USA), 2006;
30. b) S. Metobo, R. M. Williams, unpublished results.
31. Y. Tamura, T. Yakura, H. Tohma, K. Kikuchi, Y. Kita, Synthesis 1989, 126-127.
32. P. J. Beeby, Tetrahedron Lett. 1977, 18, 3379-3382.
33. B. Hartmann, A. M. Kanazawa, J.-P. Depres, A. E. Greene, Tetrahedron Lett. 1991, 32, 5077-5080.
34. a) N. Saito, Y. Ohira, N. Wada, A. Kubo, Tetrahedron 1990, 46, 7711-7728;
35. b) N. Saito, Y. Ohira, A. Kubo, Chem. Pharm. Bull. 1990, 38, 821-823;
36. c) N. Saito, M. Nishida, A. Kubo, Chem. Pharm. Bull. 1991, 39, 1343-1345.
37. D. B. Dess, J. C Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287.
38. N. Saito, S. Harada, M. Nishida, I. Inouye, A. Kubo, Chem. Pharm. Bull. 1995, 43, 777-782.