SCOPUS 정보 검색 플랫폼

Tetrahedron Asymmetry

Volumn 23, Issue 10, 2012, Pages 742-747

A novel and high-yielding asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from (-)-shikimic acid

(5) Nie, Liang Deng a Ding, Wei a Shi, Xiao Xin a Quan, Na a Lu, Xia a

a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY (China)

Author keywords

[No Author keywords available]

Indexed keywords

OSELTAMIVIR; PHOSPHINE DERIVATIVE; REAGENT; SHIKIMIC ACID; TRIPHENYLPHOSPINE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL COMPOSITION; CHEMICAL PROCEDURES; CHEMICAL REACTION; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 84863003128 PISSN: 09574166 EISSN: 1362511X Source Type: Journal
DOI: 10.1016/j.tetasy.2012.05.014 Document Type: Article

Times cited : (27)

References (67)

1
- 15444353753
- C.U. Kim, W. Lew, M.A. Williams, H. Wu, L. Zhang, X. Chen, P.A. Escarpe, D.B. Mendel, W.G. Laver, and R.C. Stevens J. Med. Chem. 41 1998 2451
- (1998) J. Med. Chem. , vol.41 , pp. 2451
- Kim, C.U.¹ Lew, W.² Williams, M.A.³ Wu, H.⁴ Zhang, L.⁵ Chen, X.⁶ Escarpe, P.A.⁷ Mendel, D.B.⁸ Laver, W.G.⁹ Stevens, R.C.¹⁰

2
- 0031048319
- C.U. Kim, W. Lew, M.A. Williams, H. Liu, L. Zhang, S. Swaminathan, N. Bischofberger, M.S. Chen, D.B. Mendel, C.Y. Tai, W.G. Laver, and R.C. Stevens J. Am. Chem. Soc. 119 1997 681
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 681
- Kim, C.U.¹ Lew, W.² Williams, M.A.³ Liu, H.⁴ Zhang, L.⁵ Swaminathan, S.⁶ Bischofberger, N.⁷ Chen, M.S.⁸ Mendel, D.B.⁹ Tai, C.Y.¹⁰ Laver, W.G.¹¹ Stevens, R.C.¹²

3
- 33847038372
- A.C. Hurt, P. Selleck, N. Komadina, R. Shaw, L. Brown, and I.G. Barr Antiviral Res. 73 2007 228
- (2007) Antiviral Res. , vol.73 , pp. 228
- Hurt, A.C.¹ Selleck, P.² Komadina, N.³ Shaw, R.⁴ Brown, L.⁵ Barr, I.G.⁶

4
- 19544391228
- A. Abbott Nature 435 2005 407
- (2005) Nature , vol.435 , pp. 407
- Abbott, A.¹

5
- 0035823244
- G. Laver, and E. Garman Science 293 2001 1776
- (2001) Science , vol.293 , pp. 1776
- Laver, G.¹ Garman, E.²

6
- 77953262416
- J.D. Bloom, L.L. Gong, and D. Baltimore Science 328 2010 1272
- (2010) Science , vol.328 , pp. 1272
- Bloom, J.D.¹ Gong, L.L.² Baltimore, D.³

7
- 80052710725
- J. Magano Tetrahedron 67 2011 7875
- (2011) Tetrahedron , vol.67 , pp. 7875
- Magano, J.¹

8
- 79953871636
- M. Shibasaki, M. Kanai, and K. Yamatsugu Isr. J. Chem. 51 2011 316
- (2011) Isr. J. Chem. , vol.51 , pp. 316
- Shibasaki, M.¹ Kanai, M.² Yamatsugu, K.³

9
- 70349095283
- J. Magano Chem. Rev. 109 2009 4398
- (2009) Chem. Rev. , vol.109 , pp. 4398
- Magano, J.¹

10
- 46849088854
- M. Shibasaki, and M. Kanai Eur. J. Org. Chem. 1839 2008
- (2008) Eur. J. Org. Chem. , vol.1839
- Shibasaki, M.¹ Kanai, M.²

11
- 61549140440
- J. Gong, and W. Xu Curr. Med. Chem. 15 2008 3145
- (2008) Curr. Med. Chem. , vol.15 , pp. 3145
- Gong, J.¹ Xu, W.²

12
- 34247465181
- S. Abrecht, M.C. Federspiel, H. Estermann, R. Fischer, M. Karpf, H.-J. Mair, T. Oberhauser, G. Rimmler, R. Trussardi, and U. Zutter Chimia 61 2007 93
- (2007) Chimia , vol.61 , pp. 93
- Abrecht, S.¹ Federspiel, M.C.² Estermann, H.³ Fischer, R.⁴ Karpf, M.⁵ Mair, H.-J.⁶ Oberhauser, T.⁷ Rimmler, G.⁸ Trussardi, R.⁹ Zutter, U.¹⁰

13
- 33751254092
- V. Farina, and J.D. Brown Angew. Chem., Int. Ed. 45 2006 7330
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 7330
- Farina, V.¹ Brown, J.D.²

14
- 6444232887
- S. Abrecht, P. Harrington, H. Iding, M. Karpf, R. Trussardi, B. Wirz, and U. Zutter Chimia 58 2004 621
- (2004) Chimia , vol.58 , pp. 621
- Abrecht, S.¹ Harrington, P.² Iding, H.³ Karpf, M.⁴ Trussardi, R.⁵ Wirz, B.⁶ Zutter, U.⁷

15
- 80054050185
- H. Ishikawa, B.P. Bondzic, and Y. Hayashi Eur. J. Org. Chem. 2011 6020
- (2011) Eur. J. Org. Chem. , pp. 6020
- Ishikawa, H.¹ Bondzic, B.P.² Hayashi, Y.³

16
- 84857457239
- D.S. Gunasekera Synlett 2012 573
- (2012) Synlett , pp. 573
- Gunasekera, D.S.¹

17
- 84862776937
- H.-K. Kim, and K.-J. Jenny Park Tetrahedron Lett. 53 2012 1561
- (2012) Tetrahedron Lett. , vol.53 , pp. 1561
- Kim, H.-K.¹ Jenny Park, K.-J.²

18
- 79952586610
- B.M. Trost, and T. Zhang Chem. Eur. J. 17 2011 3630
- (2011) Chem. Eur. J. , vol.17 , pp. 3630
- Trost, B.M.¹ Zhang, T.²

19
- 84055193839
- L. Werner, A. Machara, B. Sullivan, I. Carrera, M. Moser, D.R. Adams, T. Hudlicky, and J. Andraos J. Org. Chem. 76 2011 10050
- (2011) J. Org. Chem. , vol.76 , pp. 10050
- Werner, L.¹ MacHara, A.² Sullivan, B.³ Carrera, I.⁴ Moser, M.⁵ Adams, D.R.⁶ Hudlicky, T.⁷ Andraos, J.⁸

20
- 79959667209
- T. Tanaka, Q. Tan, H. Kawakubo, and M. Hayashi J. Org. Chem. 76 2011 5477
- (2011) J. Org. Chem. , vol.76 , pp. 5477
- Tanaka, T.¹ Tan, Q.² Kawakubo, H.³ Hayashi, M.⁴

21
- 81155134626
- L.-D. Nie, X.-X. Shi, N. Quan, F.-F. Wang, and X. Lu Tetrahedron: Asymmetry 22 2011 1692
- (2011) Tetrahedron: Asymmetry , vol.22 , pp. 1692
- Nie, L.-D.¹ Shi, X.-X.² Quan, N.³ Wang, F.-F.⁴ Lu, X.⁵

22
- 79952038512
- S. Raghavan, and V.S. Babu Tetrahedron 67 2011 2044
- (2011) Tetrahedron , vol.67 , pp. 2044
- Raghavan, S.¹ Babu, V.S.²

23
- 77953955584
- S. Zhu, S. Yu, Y. Wang, and D. Ma Angew. Chem., Int. Ed. 49 2010 4656
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 4656
- Zhu, S.¹ Yu, S.² Wang, Y.³ Ma, D.⁴

24
- 77957840549
- H. Ishikawa, T. Suzuki, H. Orita, T. Uchimaru, and Y. Hayashi Chem. Eur. J. 16 2010 12616
- (2010) Chem. Eur. J. , vol.16 , pp. 12616
- Ishikawa, H.¹ Suzuki, T.² Orita, H.³ Uchimaru, T.⁴ Hayashi, Y.⁵

25
- 77950789587
- J. Ma, Y. Zhao, S. Ng, J. Zhang, J. Zeng, A. Than, P. Chen, and X.-W. Liu Chem. Eur. J. 16 2010 4533
- (2010) Chem. Eur. J. , vol.16 , pp. 4533
- Ma, J.¹ Zhao, Y.² Ng, S.³ Zhang, J.⁴ Zeng, J.⁵ Than, A.⁶ Chen, P.⁷ Liu, X.-W.⁸

26
- 75749139716
- L. Werner, A. Machara, and T. Hudlicky Adv. Synth. Catal. 352 2010 195
- (2010) Adv. Synth. Catal. , vol.352 , pp. 195
- Werner, L.¹ MacHara, A.² Hudlicky, T.³

27
- 73949112374
- H. Osato, I.L. Jones, A. Chen, and C.L.L. Chai Org. Lett. 12 2010 60
- (2010) Org. Lett. , vol.12 , pp. 60
- Osato, H.¹ Jones, I.L.² Chen, A.³ Chai, C.L.L.⁴

28
- 79952201998
- J.S. Ko, J.E. Keum, and S.Y. Ko J. Org. Chem. 75 2010 7006
- (2010) J. Org. Chem. , vol.75 , pp. 7006
- Ko, J.S.¹ Keum, J.E.² Ko, S.Y.³

29
- 77951866321
- A. Kamimura, and T. Nakano J. Org. Chem. 75 2010 3133
- (2010) J. Org. Chem. , vol.75 , pp. 3133
- Kamimura, A.¹ Nakano, T.²

30
- 77951780307
- J. Weng, Y.-B. Li, R.-B. Wang, F.-Q. Li, C. Liu, A.S.C. Chan, and G. Lu J. Org. Chem. 75 2010 3125
- (2010) J. Org. Chem. , vol.75 , pp. 3125
- Weng, J.¹ Li, Y.-B.² Wang, R.-B.³ Li, F.-Q.⁴ Liu, C.⁵ Chan, A.S.C.⁶ Lu, G.⁷

31
- 77953229556
- P. Wichienukul, S. Akkarasamiyo, N. Kongkathip, and B. Kongkathip Tetrahedron Lett. 51 2010 3208
- (2010) Tetrahedron Lett. , vol.51 , pp. 3208
- Wichienukul, P.¹ Akkarasamiyo, S.² Kongkathip, N.³ Kongkathip, B.⁴

32
- 78651322087
- Z. Hong, Q. Cui, J. Peng, H. Hu, and Z. Chen Chin. J. Chem. 28 2010 2479
- (2010) Chin. J. Chem. , vol.28 , pp. 2479
- Hong, Z.¹ Cui, Q.² Peng, J.³ Hu, H.⁴ Chen, Z.⁵

33
- 70350072245
- M. Karpf, and R. Trussardi Angew. Chem., Int. Ed. 48 2009 5760
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5760
- Karpf, M.¹ Trussardi, R.²

34
- 70349778974
- B. Sullivan, I. Carrera, M. Drouin, and T. Hudlicky Angew. Chem., Int. Ed. 48 2009 4229
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 4229
- Sullivan, B.¹ Carrera, I.² Drouin, M.³ Hudlicky, T.⁴

35
- 60149095699
- H. Ishikawa, T. Suzuki, and Y. Hayashi Angew. Chem., Int. Ed. 48 2009 1304
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 1304
- Ishikawa, H.¹ Suzuki, T.² Hayashi, Y.³

36
- 59049090575
- K. Yamatsugu, L. Yin, S. Kamijo, Y. Kimura, M. Kanai, and M. Shibasaki Angew. Chem., Int. Ed. 48 2009 1070
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 1070
- Yamatsugu, K.¹ Yin, L.² Kamijo, S.³ Kimura, Y.⁴ Kanai, M.⁵ Shibasaki, M.⁶

37
- 61349156679
- L.-D. Nie, and X.-X. Shi Tetrahedron: Asymmetry 20 2009 124
- (2009) Tetrahedron: Asymmetry , vol.20 , pp. 124
- Nie, L.-D.¹ Shi, X.-X.²

38
- 65949109696
- L.-D. Nie, X.-X. Shi, K.H. Ko, and W.-D. Lu J. Org. Chem. 74 2009 3970
- (2009) J. Org. Chem. , vol.74 , pp. 3970
- Nie, L.-D.¹ Shi, X.-X.² Ko, K.H.³ Lu, W.-D.⁴

39
- 67649363486
- K. Yamatsugu, M. Kanai, and M. Shibasaki Tetrahedron 65 2009 6017
- (2009) Tetrahedron , vol.65 , pp. 6017
- Yamatsugu, K.¹ Kanai, M.² Shibasaki, M.³

40
- 62049086267
- N. Satoh, T. Akiba, S. Yokoshima, and T. Fukuyama Tetrahedron 65 2009 3239
- (2009) Tetrahedron , vol.65 , pp. 3239
- Satoh, N.¹ Akiba, T.² Yokoshima, S.³ Fukuyama, T.⁴

41
- 65549152349
- Y. Kimura, K. Yamatsugu, M. Kanai, N. Echigo, T. Kuzuhara, and M. Shibasaki Tetrahedron Lett. 50 2009 3205
- (2009) Tetrahedron Lett. , vol.50 , pp. 3205
- Kimura, Y.¹ Yamatsugu, K.² Kanai, M.³ Echigo, N.⁴ Kuzuhara, T.⁵ Shibasaki, M.⁶

42
- 62349105131
- T. Oshitari, and T. Mandai Synlett 2009 787
- (2009) Synlett , pp. 787
- Oshitari, T.¹ Mandai, T.²

43
- 62349109401
- T. Mandai, and T. Oshitari Synlett 2009 783
- (2009) Synlett , pp. 783
- Mandai, T.¹ Oshitari, T.²

44
- 70449394161
- H. Sun, Y.-J. Lin, Y.-L. Wu, and Y. Wu Synlett 2009 2473
- (2009) Synlett , pp. 2473
- Sun, H.¹ Lin, Y.-J.² Wu, Y.-L.³ Wu, Y.⁴

45
- 53549123019
- J.-J. Shie, J.-M. Fang, and C.-H. Wong Angew. Chem., Int. Ed. 47 2008 5788
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 5788
- Shie, J.-J.¹ Fang, J.-M.² Wong, C.-H.³

46
- 45549100945
- B.M. Trost, and T. Zhang Angew. Chem., Int. Ed. 47 2008 3759
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3759
- Trost, B.M.¹ Zhang, T.²

47
- 43549123603
- N.T. Kipassa, H. Okamura, K. Kina, T. Hamada, and T. Iwagawa Org. Lett. 10 2008 815
- (2008) Org. Lett. , vol.10 , pp. 815
- Kipassa, N.T.¹ Okamura, H.² Kina, K.³ Hamada, T.⁴ Iwagawa, T.⁵

48
- 46849084792
- U. Zutter, H. Iding, P. Spurr, and B. Wirz J. Org. Chem. 73 2008 4895
- (2008) J. Org. Chem. , vol.73 , pp. 4895
- Zutter, U.¹ Iding, H.² Spurr, P.³ Wirz, B.⁴

49
- 54049095827
- M. Matveenko, A.C. Willis, and M.G. Banwell Tetrahedron Lett. 49 2008 7018
- (2008) Tetrahedron Lett. , vol.49 , pp. 7018
- Matveenko, M.¹ Willis, A.C.² Banwell, M.G.³

50
- 38149121471
- M. Morita, T. Sone, K. Yamatsugu, Y. Sohtome, S. Matsunaga, M. Kanai, Y. Watanabe, and M. Shibasaki Bioorg. Med. Chem. Lett. 18 2008 600
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 600
- Morita, M.¹ Sone, T.² Yamatsugu, K.³ Sohtome, Y.⁴ Matsunaga, S.⁵ Kanai, M.⁶ Watanabe, Y.⁷ Shibasaki, M.⁸

51
- 34848839869
- J.-J. Shie, J.-M. Fang, S.-Y. Wang, K.-C. Tsai, Y.-S.E. Cheng, A.-S. Yang, S.-C. Hsiao, C.-Y. Su, and C.-H. Wong J. Am. Chem. Soc. 129 2007 11892
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 11892
- Shie, J.-J.¹ Fang, J.-M.² Wang, S.-Y.³ Tsai, K.-C.⁴ Cheng, Y.-S.E.⁵ Yang, A.-S.⁶ Hsiao, S.-C.⁷ Su, C.-Y.⁸ Wong, C.-H.⁹

52
- 34547445036
- N. Satoh, T. Akiba, S. Yokoshima, and T. Fukuyama Angew. Chem., Int. Ed. 46 2007 5734
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 5734
- Satoh, N.¹ Akiba, T.² Yokoshima, S.³ Fukuyama, T.⁴

53
- 34547465233
- K.M. Bromfield, H. Graden, D.P. Hagberg, T. Olsson, and N. Kann Chem. Commun. 2007 3183
- (2007) Chem. Commun. , pp. 3183
- Bromfield, K.M.¹ Graden, H.² Hagberg, D.P.³ Olsson, T.⁴ Kann, N.⁵

54
- 33846647467
- T. Mita, N. Fukuda, F.X. Roca, M. Kanai, and M. Shibasaki Org. Lett. 9 2007 259
- (2007) Org. Lett. , vol.9 , pp. 259
- Mita, T.¹ Fukuda, N.² Roca, F.X.³ Kanai, M.⁴ Shibasaki, M.⁵

55
- 33846340028
- K. Yamatsugu, S. Kamijo, Y. Suto, M. Kanai, and M. Shibasaki Tetrahedron Lett. 48 2007 1403
- (2007) Tetrahedron Lett. , vol.48 , pp. 1403
- Yamatsugu, K.¹ Kamijo, S.² Suto, Y.³ Kanai, M.⁴ Shibasaki, M.⁵

56
- 33646560979
- Y. Fukuta, T. Mita, N. Fukuda, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 128 2006 6312
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 6312
- Fukuta, Y.¹ Mita, T.² Fukuda, N.³ Kanai, M.⁴ Shibasaki, M.⁵

57
- 33646567839
- Y.-Y. Yeung, S. Hong, and E.J. Corey J. Am. Chem. Soc. 128 2006 6310
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 6310
- Yeung, Y.-Y.¹ Hong, S.² Corey, E.J.³

58
- 33745700294
- X. Cong, and Z.-J. Yao J. Org. Chem. 71 2006 5365
- (2006) J. Org. Chem. , vol.71 , pp. 5365
- Cong, X.¹ Yao, Z.-J.²

59
- 0842306928
- P.J. Harrington, J.D. Brown, T. Foderaro, and R.C. Hughes Org. Process Res. Dev. 8 2004 86
- (2004) Org. Process Res. Dev. , vol.8 , pp. 86
- Harrington, P.J.¹ Brown, J.D.² Foderaro, T.³ Hughes, R.C.⁴

60
- 0035937274
- M. Karpf, and R. Trussardi J. Org. Chem. 66 2001 2044
- (2001) J. Org. Chem. , vol.66 , pp. 2044
- Karpf, M.¹ Trussardi, R.²

61
- 0033435755
- M. Federspiel, R. Fischer, M. Hennig, H.-J. Mair, T. Oberhauser, G. Rimmler, T. Albiez, J. Bruhin, H. Estermann, C. Gandert, V. Gockel, S. Gotzo, U. Hoffmann, G. Huber, G. Janatsch, S. Lauper, O. Rockel-Stabler, R. Trussardi, and A.G. Zwahlen Org. Process Res. Dev. 3 1999 266
- (1999) Org. Process Res. Dev. , vol.3 , pp. 266
- Federspiel, M.¹ Fischer, R.² Hennig, M.³ Mair, H.-J.⁴ Oberhauser, T.⁵ Rimmler, G.⁶ Albiez, T.⁷ Bruhin, J.⁸ Estermann, H.⁹ Gandert, C.¹⁰ Gockel, V.¹¹ Gotzo, S.¹² Hoffmann, U.¹³ Huber, G.¹⁴ Janatsch, G.¹⁵ Lauper, S.¹⁶ Rockel-Stabler, O.¹⁷ Trussardi, R.¹⁸ Zwahlen, A.G.¹⁹

62
- 0032568893
- J.C. Rohloff, K.M. Kent, M.J. Postich, M.W. Becker, H.H. Chapman, D.E. Kelly, W. Lew, M.S. Louie, L.R. McGee, E.J. Prisbe, L.M. Schultze, R.H. Yu, and L. Zhang J. Org. Chem. 63 1998 4545
- (1998) J. Org. Chem. , vol.63 , pp. 4545
- Rohloff, J.C.¹ Kent, K.M.² Postich, M.J.³ Becker, M.W.⁴ Chapman, H.H.⁵ Kelly, D.E.⁶ Lew, W.⁷ Louie, M.S.⁸ McGee, L.R.⁹ Prisbe, E.J.¹⁰ Schultze, L.M.¹¹ Yu, R.H.¹² Zhang, L.¹³

63
- 68949208418
- H. Ohira, N. Torii, T.M. Aida, M. Watanabe, and R.L. Smith Sep. Purif. Technol. 69 2009 102
- (2009) Sep. Purif. Technol. , vol.69 , pp. 102
- Ohira, H.¹ Torii, N.² Aida, T.M.³ Watanabe, M.⁴ Smith, R.L.⁵

64
- 65949090708
- X.-H. He, L. Liu, X.-G. Liu, Z.-P. Liu, G.-M. Zhao, and H.-Y. Li Nat. Prod. Res. Dev. (in Chinese) 20 2008 914
- (2008) Nat. Prod. Res. Dev. (In Chinese) , vol.20 , pp. 914
- He, X.-H.¹ Liu, L.² Liu, X.-G.³ Liu, Z.-P.⁴ Zhao, G.-M.⁵ Li, H.-Y.⁶

65
- 40849104789
- L.B. Enrich, M.L. Scheuermann, A. Mohadjer, K.R. Matthias, C.F. Eller, M.S. Newman, M. Fujinaka, and T. Poon Tetrahedron Lett. 49 2008 2503
- (2008) Tetrahedron Lett. , vol.49 , pp. 2503
- Enrich, L.B.¹ Scheuermann, M.L.² Mohadjer, A.³ Matthias, K.R.⁴ Eller, C.F.⁵ Newman, M.S.⁶ Fujinaka, M.⁷ Poon, T.⁸

66
- 41049109869
- R. Sui Chem. Eng. Technol. 31 2008 469
- (2008) Chem. Eng. Technol. , vol.31 , pp. 469
- Sui, R.¹

67
- 0344609866
- K.M. Draths, D.R. Knop, and J.W. Frost J. Am. Chem. Soc. 121 1999 1603
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 1603
- Draths, K.M.¹ Knop, D.R.² Frost, J.W.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.