A C 2-symmetric pool based flexible strategy: An enantioconvergent synthesis of (+)-valiolamine and (+)-valienamine

European Journal of Organic Chemistry

Volumn , Issue 14, 2012, Pages 2780-2785

  Lo, Hong Jay ^a   Chen, Cheng Yih ^a   Zheng, Wei Lin ^a   Yeh, Shang Ming ^a   Yan, Tu Hsin ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

Amino pseudosugars; Chiral pool; Cyclization; Inhibitors; Natural products

Indexed keywords

EID: 84860634639     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201101845     Document Type: Article

References (38)

1. X. Chen, Y. Fan, Y. Zheng, Y. Shen, Chem. Rev. 2003, 103, 1955.
2. T. Mahmud, Nat. Prod. Rep. 2003, 20, 137.
3. S. Horri, H. Fufase, T. Matsuo, N. Asano, K. Matsui, J. Med. Chem. 1986, 29, 1038.
4. Y. Kameda, N. Asano, M. Yoshikawa, M. Takeuchi, T. Yamaguchi, K. Matsui, J. Antibiot. 1984, 37, 1301.
5. Y. Kameda, N. Asano, M. Yoshikawa, K. Mabui, S. Horii, H. Fukawase, J. Antibiot. 1983, 36, 1157.
6. Y. Kameda, N. Asano, M. Teranoshi, K. Amatsui, J. Antibiot. 1980, 33, 1573.
7. T. Suami, S. Ogawa, Adv. Carbohydr. Chem. Biochem. 1990, 48, 22.
8. T. K. M. Shing, L. H. Wan, Angew. Chem. 1995, 107, 1742
9. Angew. Chem. Int. Ed. Engl. 1995, 34, 1643.
10. T. K. M. Shing, H. M. Cheng, Org. Lett. 2008, 10, 4137.
11. T. K. M. Shing, L. H. Wan, J. Org. Chem. 1996, 61, 8468.
12. B. M. Trost, L. S. Chupak, T. J. Lubbers, J. Am. Chem. Soc. 1998, 120, 1732.
13. H. Paulsen, F. R. Heiker, Angew. Chem. 1980, 92, 930;
14. Angew. Chem. Int. Ed. Engl. 1980, 19, 904.
15. R. R. Schmidt, A. Kohn, Angew. Chem. 1987, 99, 490;
16. Angew. Chem. Int. Ed. Engl. 1987, 26, 482.
17. H. Fukase, S. Horii, J. Org. Chem. 1992, 57, 3651.
18. Y.-K. Chang, B.-Y. Lee, D.-J. Kim, G.-S. Lee, H.-B. Jeon, K.-S. Kim, J. Org. Chem. 2005, 70, 3299.
19. P. Kapferer, F. Sarabia, A. Vasella, Helv. Chim. Acta 1999, 82, 645.
20. S. H. L. Kok, C.-C. Lee, T. K. M. Shing, J. Org. Chem. 2001, 66, 7184.
21. T. K. M. Shing, T.-Y. Li, S. H. L. Kok, J. Org. Chem. 1999, 64, 1941.
22. for an enantiospecific synthesis of bis-valienamine from (-)-quinic acid, see:, T. K. M. Shing, C. S. K. Kwong, A. W. C. Cheung, S. H.-L. Kok, Z. Yu, J. Li, C. H. K. Cheng, J. Am. Chem. Soc. 2004, 126, 15990.
23. W.-D. Lee, K. Kim, G. A. Sulikowski, Org. Lett. 2005, 7, 1687.
24. C. Gaul, J. T. Njardarson, D. Shan, D. C. Dorn, K.-D. Wu, W. P. Tong, X.-Y. Huang, M. A. S. Moore, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 11326.
25. C. Gaul, J. T. Njardarson, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 6042.
26. R. M. Conrad, M. J. Grogan, C. R. Bertozzi, Org. Lett. 2002, 4, 1359.
27. M. Jorgensen, E. H. Iversen, A. L. Paulsen, R. Madsen, J. Org. Chem. 2001, 66, 4630.
28. L. Hyldtoft, R. Madsen, J. Am. Chem. Soc. 2000, 122, 8444.
29. D. F. Taber, A. Sahli, H. Yu, R. P. Meagley, J. Org. Chem. 1995, 60, 6571.
30. for a one-pot conversion of inexpensive tartaric acid to tartrate, see:, E. A. Mash, K. A. Nelson, S. V. Deusen, S. B. Hemperly, Org. Synth. 1990, 68, 92.
31. S. P. Khanapure, N. Najafi, S. Manna, J.-J. Yang, J. Rokach, J. Org. Chem. 1995, 60, 7548.
32. Y.-K. Chang, H.-J. Lo, T.-H. Yan, Org. Lett. 2009, 11, 4278.
33. 2 symmetry and asymmetric induction, see:, J. K. Whitesell, Chem. Rev. 1989, 89, 1581.
34. S. Knapp, D. V. Patel, J. Org. Chem. 1984, 49, 5072.
35. R. G. Barnhardt Jr., W. E. McEwen, J. Am. Chem. Soc. 1967, 89, 7009.
36. H. Becker, K. B. Sharpless, Angew. Chem. 1996, 108, 447;
37. Angew. Chem. Int. Ed. Engl. 1996, 35, 448.
38. S. Ogawa, Y. Ohishi, M. Asada, A. Tomoda, A. Takahashi, Y. Ooki, M. Mori, T. Korenaga, Org. Biomol. Chem. 2004, 2, 884.