Total synthesis of (+)-valienamine and (-)-1-epi-valienamine via a highly diastereoselective allylic amination of cyclic polybenzyl ether using chlorosulfonyl isocyanate

Tetrahedron

Volumn 69, Issue 48, 2013, Pages 10384-10390

  Li, Qing Ri ^a   Kim, Seung In ^a   Park, Sook Jin ^a   Yang, Hye Ran ^a   Baek, A Reum ^a   Kim, In Su ^a   Jung, Young Hoon ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Amination; Asymmetric; Carbasugar; Chlorosulfonyl isocyanate; Valienamine

Indexed keywords

1 EPI VALIENAMINE; AMINE; BENZYL DERIVATIVE; ISOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VALIDOXYLAMINE A; VALIENAMINE;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; BENZYLATION; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY; WITTIG REACTION;

EID: 84887049307     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.09.098     Document Type: Article

References (46)

1. N. Asano Curr. Top. Med. Chem. 3 2003 471
2. A.D. Elbein FASEB J. 5 1991 3055
3. N. Asano, R.J. Nash, R.J. Molyneux, and G.W.J. Fleet Tetrahedron: Asymmetry 11 2000 1645
4. L. Somsák, V. Nagya, Z. Hadady, T. Docsa, and P. Gergely Curr. Pharm. Des. 9 2003 1177
5. P.S. Johnson, H.E. Lebovitz, R.F. Coniff, D.C. Simonson, P. Raskin, and C.L. Munera J. Clin. Endocrinol. Metab. 83 1998 1515
6. P. Greimel, J. Spreitz, A.E. Stütz, and T.M. Wrodnigg Curr. Top. Med. Chem. 3 2003 513
7. G.W.J. Fleet, A. Karpas, R.A. Dwek, L.E. Fellows, A.S. Tyms, S. Peturrson, S.K. Namgoong, N.G. Ramsden, P.W. Smith, J.C. Son, F. Wilson, D.R. Witty, G.S. Jacob, and T.W. Rademacher FEBS Lett. 237 1988 128
8. Bitonti, A. J.; Sjoersma, A.; McCann, P. P. Eur. Patent Appl. EP423728, 1991.
9. Y. Nishimura Curr. Top. Med. Chem. 3 2003 575
10. G.K. Ostrander, N.K. Scribner, and L.R. Rohrschneider Cancer Res. 48 1988 1091
11. T. Tsuruoka, H. Fukuyasu, M. Ishii, T. Usui, S. Shibahara, and S. Inouye J. Antibiot. 49 1996 155
12. Y. Kameda, and S. Horii J. Chem. Soc., Chem. Commun. 1972 746
13. Y. Kameda, N. Asano, M. Teranishi, and K. Matsui J. Antibiot. 33 1980 1573
14. Y. Kameda, N. Asano, M. Teranishi, M. Yoshikawa, and K. Matsui J. Antibiot. 34 1981 1237
15. N. Asano, M. Takeuchi, K. Ninomiya, Y. Kameda, and K. Matsui J. Antibiot. 37 1984 859
16. S. Ogawa, Y. Miyamoto, and A. Nakajima Chem. Lett. 1989 725
17. S. Ogawa, A. Nakajima, and Y. Miyamoto J. Chem. Soc., Perkin Trans. 1 1991 3287
18. T. Mahmud Nat. Prod. Rep. 20 2003 137
19. D. Schmidt, W. Frommer, B. Junge, K. Müller, W. Wingender, and E. Trutsheit Naturwissenschaften 64 1977 536
20. H. Paulsen, and F.R. Heiker Angew. Chem., Int. Ed. Engl. 19 1980 904
21. H. Fukase, and S. Horii J. Org. Chem. 57 1992 3651
22. P. Kapferer, F. Sarabia, and A. Vasella Helv. Chim. Acta 82 1999 645
23. Y.-K. Chang, B.-Y. Lee, D.-J. Kim, G.-S. Lee, H.-B. Jeon, and K.-S. Kim J. Org. Chem. 70 2005 3299
24. Y.-K. Chang, H.-J. Lo, and T.-H. Yan Org. Lett. 11 2009 4278
25. H.-J. Lo, C.-Y. Chen, W.-L. Zheng, S.-M. Yeh, and T.-H. Yan Eur. J. Org. Chem. 2012 2780 For a selected example on formal synthesis of 1, see
26. I. Cumpstey Tetrahedron Lett. 46 2005 6257
27. P.R. Krishna, and P.S. Reddy Synlett 2009 209
28. B. Zhou, Z. Luo, S. Lin, and Y. Li Synlett 2012 913
29. T.K.M. Shing, T.-Y. Li, and S.H.L. Kok J. Org. Chem. 64 1999 1941
30. S.H.L. Kok, C.-C. Lee, and T.K.M. Shing J. Org. Chem. 66 2001 7184
31. S. Ogawa, Y. Shibata, T. Nose, and T. Suami Bull. Chem. Soc. Jpn. 58 1985 3387
32. S. Knapp, A.B.J. Naughton, and T.G.M. Dhar Tetrahedron Lett. 33 1992 1025
33. B.M. Trost, L.S. Chupak, and T. Lubbers J. Am. Chem. Soc. 120 1998 1732
34. I.S. Kim, and Y.H. Jung Heterocycles 83 2011 2489 For recent examples, see
35. I.S. Kim, Q.R. Li, J.K. Lee, S.H. Lee, J.K. Lim, O.P. Zee, and Y.H. Jung Synlett 2007 1711
36. I.S. Kim, H.Y. Lee, and Y.H. Jung Heterocycles 71 2007 1787
37. I.S. Kim, C.B. Ryu, Q.R. Li, O.P. Zee, and Y.H. Jung Tetrahedron Lett. 48 2007 6258
38. I.S. Kim, Q.R. Li, G.R. Dong, S.H. Woo, H.-j. Park, O.P. Zee, and Y.H. Jung Synlett 2008 2985
39. I.S. Kim, Q.R. Li, G.R. Dong, Y.C. Kim, Y.J. Hong, M. Lee, K.-W. Chi, J.S. Oh, and Y.H. Jung Eur. J. Org. Chem. 2010 1569
40. S.H. Lee, I.S. Kim, Q.R. Li, G.R. Dong, L.S. Jeong, and Y.H. Jung J. Org. Chem. 76 2011 10011
41. G.R. Dong, S.M. Hong, S.I. Kim, I.S. Kim, and Y.H. Jung Eur. J. Org. Chem. 2012 4200
42. S.J. Kim, T.H. Jeon, I.S. Min, I.S. Kim, and Y.H. Jung Tetrahedron Lett. 53 2012 3680
43. S.H. Lee, S.J. Park, I.S. Kim, and Y.H. Jung Tetrahedron 69 2013 1877
44. I.S. Min, S.I. Kim, S. Hong, I.S. Kim, and Y.H. Jung Tetrahedron 69 2013 3901
45. B. Dasari, S. Jogula, R. Borhade, S. Balasubramanian, G. Chandrasekar, S.S. Kitambi, and P. Arya Org. Lett. 15 2013 432
46. I. Cumpstey, S. Gehrke, S. Erfan, and R. Cribiu Carbohydr. Res. 343 2008 1675