Asymmetric synthesis of antithrombotic agent M55529: The first enantioselective cyclic N,O-acetal formation

European Journal of Organic Chemistry

Volumn , Issue 10, 2006, Pages 2269-2272

  Saitoh, Fumihiko ^a,b   Nishida, Hidemitsu ^b   Mukaihira, Takafumi ^b   Aikawa, Kohsuke ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b MOCHIDA PHARMACEUTICAL CO   (Japan)

Author keywords

Antithrombotic agent; Cyclic N,O acetal; Enantioselective acetal formation; M55529

Indexed keywords

EID: 33646727644     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600124     Document Type: Article

References (42)

1. Reviews: a) P. D. Dewick, Medicinal Natural Products: A Biosynthetic Approach, Wiley, Chichester, 2002;
2. b) J. ApSimon (Ed.), The Total Synthesis of Natural Products, Wiley, New York, 1977, vol. 3;
3. c) E. J. Corey, X.-M. Cheng, The Logic of Chemical Synthesis Wiley, New York, 1989;
4. d) K. C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis, VCH, Weinheim, 1996.
5. W. T. Green, P. G. Wuts, Protecting Groups in Organic Synthesis 3rd. ed., Wiley, New York, 1999.
6. a) A. Ishii, K. Higashiyama, K. Mikami, Synlett 1997, 1381-1382;
7. b) A. Ishii, F. Miyamoto, K. Higashiyama, K. Mikami, Tetrahedron Lett. 1998, 39, 1199-1202;
8. c) A. Ishii, F. Miyamoto, K. Higashiyama, K. Mikami, Chem. Lett. 1998, 119-120;
9. d) J. Jiang, R. J. DeVita, G. A. Doss, M. T. Goulet, M. J. Wyvratt, J. Am. Chem. Soc. 1999, 121, 593-594;
10. e) N. A. Magnus, P. N. Confalone, L. Storace, Tetrahedron Lett. 2000, 41, 3015-3019;
11. f) N. Lebouvier, C. Laroche, F. Huguenot, T. Brigaud, Tetrahedron Lett. 2002, 43, 2827-2830;
12. g) F. Gosselin, A. Roy, P. D. O'Shea, C. Chen, R. P. Volante, Org. Lett. 2004, 6, 641-644;
13. h) C. K. Miao, R. Soreck, P.-J. Jones, Tetrahedron Lett. 1993, 34, 2259-2262.
14. a) N. Yamazaki, T. Kusanagi, C. Kibayashi, Tetrahedron Lett. 2004, 45, 6509-6512;
15. b) T. Itoh, N. Yamazaki, C. Kibayashi, Org. Lett. 2002, 4, 2469-2472;
16. c) N. Yamazaki, W. Dokoshi, C. Kibayashi, Org. Lett. 2001, 3, 193-196;
17. d) N. Yamazaki, T. Itoh, C. Kibayashi, Tetrahedron Lett. 1999, 40, 739-742;
18. e) M. F. Mechelke, A. I. Meyers, Tetrahedron Lett. 2000, 41, 4339-4342;
19. f) A. G. Waterson, A. I. Meyers, J. Org. Chem. 2000, 65, 7240-7243.
20. H. Nishida, T. Mukaihira, F. Saitoh, K. Harada, M. Fukui, T. Matsusue, A. Okamoto, Y. Hosaka, M. Matsumoto, I. Shiromizu, S. Ohnishi, H. Mochizuki, Chem. Pharm. Bull. 2004, 52, 406-412, and references therein.
21. a) K. Ohmori, K. Mori, Y. Ishikawa, H. Tsuruta, S. Kuwahara, N. Harada, K. Suzuki, Angew. Chem. Int. Ed. 2004, 43, 3167-3171;
22. b) Y. Kasai, H. Taji, T. Fujita, Y. Yamamoto, M. Akagi, A. Sugio, S. Kuwahara, M. Watanabe, N. Harada, A. Ichikawa, V. Schurig, Chirality 2004, 16, 569-585;
23. c) For a review see: Y. Kasai, J. Naito, S. Kuwahara, M. Watanabe, A. Ichikawa, N. Harada, Yuki Gosei Kagaku Kyokaishi 2004, 62, 1114-1127.
24. For a review see: K. Mikami, M. Terada in Lewis Acids in Organic Synthesis (Ed.: H. Yamamoto), Wiley-VCH, Weinheim, 2000, vol. 2, pp. 799-847.
25. a) R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360-12361;
26. b) E. M. Carreira, R. A. Singer, W. Lee, J. Am. Chem. Soc. 1994, 116, 8837-8838.
27. a) Rrecent reviews: T. Katsuki, Chem. Soc. Rev. 2004, 33, 437-444;
28. T. Katsuki, Adv. Synth. Catal. 2002, 344, 131-147;
29. T. Katsuki, Curr. Org. Chem. 2001, 5, 663-678;
30. b) K. Matsumoto, Y. Sawada, B. Saito, K. Sakai, T. Katsuki, Angew. Chem. Int. Ed. 2005, 44, 4935-4939;
31. c) B. Saito, T. Katsuki, Chirality 2003, 15, 24-27;
32. d) B. Saito, T. Katsuki, Tetrahedron Lett. 2002, 43, 3259-3262;
33. e) K. Aikawa, R. Irie, T. Katsuki, Tetrahedron 2001, 57, 845-851;
34. f) J. Mihara, K. Aikawa, T. Uchida, R. Irie, T. Katsuki, Heterocycles 2001, 54, 395-404;
35. g) H. Sasaki, R. Irie, T. Hamada, K. Suzuki, T. Katsuki, Tetrahedron 1994, 50, 11827-11838;
36. h) N. Hosoya, A. Hatayama, R. Irie, H. Sasaki, T. Katsuki, Tetrahedron 1994, 50, 4311-4322.
37. For recent reviews see: J. F. Larrow, E. N. Jacobsen, Topics in Organometallic Chemistry, 6 (Organometallics in Process Chemistry) 2004, 123-152;
38. T. P. Yoon, E. N. Jacobsen, Science 2003, 299(5613), 1691-1693;
39. E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421-431;
40. C. H. Sananayake, E. N. Jacobsen, Process Chemistry in the Pharmaceutical Industry 1999, 347-368;
41. M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277(5328), 936-938.
42. a was calculated by: Pallas 3.0, CompuDrug Chemistry Ltd., 1994.