SCOPUS 정보 검색 플랫폼

Chemistry - A European Journal

Volumn 20, Issue 10, 2014, Pages 2879-2887

A versatile and stereocontrolled total synthesis of dihydroxylated docosatrienes containing a conjugated E,E,Z-triene

(3) Dayaker, Gandrath a Durand, Thierry a Balas, Laurence a

a INSTITUT CHARLES GERHARDT (France)

Author keywords

lipids; medicinal chemistry; neuroprotectinD1; total synthesis; trienes

Indexed keywords

BIOMOLECULES; ESTERIFICATION; ESTERS; LIPIDS; METABOLITES; PATHOLOGY; POLYUNSATURATED FATTY ACIDS; STEREOCHEMISTRY;

DOCOSAPENTAENOIC ACID; MEDICINAL CHEMISTRY; NEUROPROTECTIND1; SONOGASHIRA CROSS-COUPLING REACTION; STEREOGENIC CENTERS; TOTAL SYNTHESIS; TRIENES; WITTIG OLEFINATION;

SYNTHESIS (CHEMICAL);

EID: 84897584628 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201304526 Document Type: Article

Times cited : (31)

References (65)

1
- 84897634349
- Online publication complete: 2 December
- L. Balas, M. Guichardant, T. Durand, M. Lagarde, Biochimie, Online publication complete: 2 December 2013, DOI:.
- (2013) Biochimie
- Balas, L.¹ Guichardant, M.² Durand, T.³ Lagarde, M.⁴

2
- 60549107724
- C. N. Serhan, R. Yang, K. Martinod, K. Kasuga, P. S. Pillai, T. F. Porter, S. F. Oh, M. Spite, J. Exp. Med. 2009, 206, 15.
- (2009) J. Exp. Med. , vol.206 , pp. 15
- Serhan, C.N.¹ Yang, R.² Martinod, K.³ Kasuga, K.⁴ Pillai, P.S.⁵ Porter, T.F.⁶ Oh, S.F.⁷ Spite, M.⁸

3
- 84860899033
- C. N. Serhan, J. Dalli, S. Karamnov, A. Choi, C. K. Park, Z. Z. Xu, R. R. Ji, M. Zhu, N. A. Petasis, FASEB J. 2012, 26, 1755.
- (2012) FASEB J. , vol.26 , pp. 1755
- Serhan, C.N.¹ Dalli, J.² Karamnov, S.³ Choi, A.⁴ Park, C.K.⁵ Xu, Z.Z.⁶ Ji, R.R.⁷ Zhu, M.⁸ Petasis, N.A.⁹

4
- 0038013967
- S. Hong, K. Gronert, P. R. Devchand, R. L. Moussignac, C. N. Serhan, J. Biol. Chem. 2003, 278, 14677.
- (2003) J. Biol. Chem. , vol.278 , pp. 14677
- Hong, S.¹ Gronert, K.² Devchand, P.R.³ Moussignac, R.L.⁴ Serhan, C.N.⁵

5
- 84861696925
- N. G. Bazan, T. N. Eady, L. Khoutorova, K. D. Atkins, S. Hong, Y. Lu, C. Zhang, B. Jun, A. Obenaus, G. Fredman, M. Zhu, J. W. Winkler, N. A. Petasis, C. N. Serhan, L. Belayev, Exp. Neurol. 2012, 236, 122.
- (2012) Exp. Neurol. , vol.236 , pp. 122
- Bazan, N.G.¹ Eady, T.N.² Khoutorova, L.³ Atkins, K.D.⁴ Hong, S.⁵ Lu, Y.⁶ Zhang, C.⁷ Jun, B.⁸ Obenaus, A.⁹ Fredman, G.¹⁰ Zhu, M.¹¹ Winkler, J.W.¹² Petasis, N.A.¹³ Serhan, C.N.¹⁴ Belayev, L.¹⁵

6
- 79955670124
- C. N. Serhan, N. A. Petasis, Chem. Rev. 2011, 111, 5922.
- (2011) Chem. Rev. , vol.111 , pp. 5922
- Serhan, C.N.¹ Petasis, N.A.²

7
- 70350334135
- P. Chen, B. Fenet, S. Michaud, N. Tomczyk, E. Vericel, M. Lagarde, M. Guichardant, FEBS Lett. 2009, 583, 3478.
- (2009) FEBS Lett. , vol.583 , pp. 3478
- Chen, P.¹ Fenet, B.² Michaud, S.³ Tomczyk, N.⁴ Vericel, E.⁵ Lagarde, M.⁶ Guichardant, M.⁷

8
- 33645507604
- I. A. Butovich, J. Lipid Res. 2006, 47, 854.
- (2006) J. Lipid Res. , vol.47 , pp. 854
- Butovich, I.A.¹

9
- 84885979109
- J. Dalli, R. A. Colas, C. N. Serhan, Sci. Rep. 2013, 3, 1940.
- (2013) Sci. Rep. , vol.3 , pp. 1940
- Dalli, J.¹ Colas, R.A.² Serhan, C.N.³

10
- 0024431893
- M. Avignon-Tropis, M. Treilhou, J. Lebreton, J. R. Pougny, I. Frechardortuno, C. Huynh, G. Linstrumelle, Tetrahedron Lett. 1989, 30, 6335.
- (1989) Tetrahedron Lett. , vol.30 , pp. 6335
- Avignon-Tropis, M.¹ Treilhou, M.² Lebreton, J.³ Pougny, J.R.⁴ Frechardortuno, I.⁵ Huynh, C.⁶ Linstrumelle, G.⁷

11
- 0025102526
- Y. Kobayashi, T. Shimazaki, H. Taguchi, F. Sato, J. Org. Chem. 1990, 55, 5324.
- (1990) J. Org. Chem. , vol.55 , pp. 5324
- Kobayashi, Y.¹ Shimazaki, T.² Taguchi, H.³ Sato, F.⁴

12
- 0032560145
- F. Babudri, V. Fiandanese, O. Hassan, A. Punzi, F. Naso, Tetrahedron 1998, 54, 4327.
- (1998) Tetrahedron , vol.54 , pp. 4327
- Babudri, F.¹ Fiandanese, V.² Hassan, O.³ Punzi, A.⁴ Naso, F.⁵

13
- 0026556577
- M. Avignon-Tropis, J. M. Berjeaud, J. R. Pougny, I. Frechardortuno, D. Guillerm, G. Linstrumelle, J. Org. Chem. 1992, 57, 651.
- (1992) J. Org. Chem. , vol.57 , pp. 651
- Avignon-Tropis, M.¹ Berjeaud, J.M.² Pougny, J.R.³ Frechardortuno, I.⁴ Guillerm, D.⁵ Linstrumelle, G.⁶

14
- 0025812346
- M. Avignon-Tropis, M. Treilhou, J. R. Pougny, I. Frechardortuno, G. Linstrumelle, Tetrahedron 1991, 47, 7279.
- (1991) Tetrahedron , vol.47 , pp. 7279
- Avignon-Tropis, M.¹ Treilhou, M.² Pougny, J.R.³ Frechardortuno, I.⁴ Linstrumelle, G.⁵

15
- 0026600196
- D. Chemin, G. Linstrumelle, Tetrahedron 1992, 48, 1943.
- (1992) Tetrahedron , vol.48 , pp. 1943
- Chemin, D.¹ Linstrumelle, G.²

16
- 0026716057
- M. Treilhou, A. Fauve, J. R. Pougny, J. C. Prome, H. Veschambre, J. Org. Chem. 1992, 57, 3203.
- (1992) J. Org. Chem. , vol.57 , pp. 3203
- Treilhou, M.¹ Fauve, A.² Pougny, J.R.³ Prome, J.C.⁴ Veschambre, H.⁵

17
- 0021144577
- K. C. Nicolaou, R. E. Zipkin, R. E. Dolle, B. D. Harris, J. Am. Chem. Soc. 1984, 106, 3548.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 3548
- Nicolaou, K.C.¹ Zipkin, R.E.² Dolle, R.E.³ Harris, B.D.⁴

18
- 0027228458
- F. A. J. Kerdesky, S. P. Schmidt, D. W. Brooks, J. Org. Chem. 1993, 58, 3516.
- (1993) J. Org. Chem. , vol.58 , pp. 3516
- Kerdesky, F.A.J.¹ Schmidt, S.P.² Brooks, D.W.³

19
- 0035056012
- A. Rodriguez, M. Nomen, B. W. Spur, J. J. Godfroid, T. H. Lee, Tetrahedron 2001, 57, 25.
- (2001) Tetrahedron , vol.57 , pp. 25
- Rodriguez, A.¹ Nomen, M.² Spur, B.W.³ Godfroid, J.J.⁴ Lee, T.H.⁵

20
- 0028288676
- K. Chauhan, R. K. Bhatt, J. R. Falck, J. H. Capdevila, Tetrahedron Lett. 1994, 35, 1825.
- (1994) Tetrahedron Lett. , vol.35 , pp. 1825
- Chauhan, K.¹ Bhatt, R.K.² Falck, J.R.³ Capdevila, J.H.⁴

21
- 0345127151
- Elsevier
- J. Rokach, Leukotrienes and Lipoxygenases: Chemical, Biological, and Clinical aspects, Vol.11, Elsevier, 1989, p. 518.
- (1989) Leukotrienes and Lipoxygenases: Chemical, Biological, and Clinical Aspects, Vol.11 , pp. 518
- Rokach, J.¹

22
- 0037136103
- S. P. Khanapure, S. Kim, J. F. Penrose, K. F. Austen, W. S. Powell, J. Rokach, Tetrahedron Lett. 2002, 43, 6063.
- (2002) Tetrahedron Lett. , vol.43 , pp. 6063
- Khanapure, S.P.¹ Kim, S.² Penrose, J.F.³ Austen, K.F.⁴ Powell, W.S.⁵ Rokach, J.⁶

23
- 51749085800
- B. M. Trost, R. C. Livingston, J. Am. Chem. Soc. 2008, 130, 11970.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 11970
- Trost, B.M.¹ Livingston, R.C.²

24
- 0019505316
- E. J. Corey, A. Marfat, J. Munroe, K. S. Kim, P. B. Hopkins, F. Brion, Tetrahedron Lett. 1981, 22, 1077.
- (1981) Tetrahedron Lett. , vol.22 , pp. 1077
- Corey, E.J.¹ Marfat, A.² Munroe, J.³ Kim, K.S.⁴ Hopkins, P.B.⁵ Brion, F.⁶

25
- 0027490653
- G. Solladié, A. Urbano, G. B. Stone, Tetrahedron Lett. 1993, 34, 6489.
- (1993) Tetrahedron Lett. , vol.34 , pp. 6489
- Solladié, G.¹ Urbano, A.² Stone, G.B.³

26
- 85013347101
- B. C. Borer, R. J. K. Taylor, Synlett 1992, 117.
- (1992) Synlett , pp. 117
- Borer, B.C.¹ Taylor, R.J.K.²

27
- 84857790197
- N. A. Petasis, R. Yang, J. W. Winkler, M. Zhu, J. Uddin, N. G. Bazan, C. N. Serhan, Tetrahedron Lett. 2012, 53, 1695.
- (2012) Tetrahedron Lett. , vol.53 , pp. 1695
- Petasis, N.A.¹ Yang, R.² Winkler, J.W.³ Zhu, M.⁴ Uddin, J.⁵ Bazan, N.G.⁶ Serhan, C.N.⁷

28
- 79955667296
- N. Ogawa, Y. Kobayashi, Tetrahedron Lett. 2011, 52, 3001.
- (2011) Tetrahedron Lett. , vol.52 , pp. 3001
- Ogawa, N.¹ Kobayashi, Y.²

29
- 79251484672
- K. Sasaki, D. Urabe, H. Arai, M. Arita, M. Inoue, Chem. Asian J. 2011, 6, 534.
- (2011) Chem. Asian J. , vol.6 , pp. 534
- Sasaki, K.¹ Urabe, D.² Arai, H.³ Arita, M.⁴ Inoue, M.⁵

30
- 84863618373
- A. R. Rodriguez, B. W. Spur, Tetrahedron Lett. 2012, 53, 4169.
- (2012) Tetrahedron Lett. , vol.53 , pp. 4169
- Rodriguez, A.R.¹ Spur, B.W.²

31
- 0036007058
- C. Gauthier, D. Castet, Y. Ramondenc, G. Ple, J. Chem. Soc. Perkin Trans. 1 2002, 191.
- (2002) J. Chem. Soc. Perkin Trans. 1 , pp. 191
- Gauthier, C.¹ Castet, D.² Ramondenc, Y.³ Ple, G.⁴

32
- 0034728204
- M. Nazaré, H. Waldmann, Tetrahedron Lett. 2000, 41, 625.
- (2000) Tetrahedron Lett. , vol.41 , pp. 625
- Nazaré, M.¹ Waldmann, H.²

33
- 0035800489
- M. Nazaré, H. Waldmann, Chem. Eur. J. 2001, 7, 3363.
- (2001) Chem. Eur. J. , vol.7 , pp. 3363
- Nazaré, M.¹ Waldmann, H.²

34
- 32244449191
- O. Dirat, A. Clipson, J. M. Elliott, S. Garrett, A. B. Jones, M. Reader, D. Shaw, Tetrahedron Lett. 2006, 47, 1729.
- (2006) Tetrahedron Lett. , vol.47 , pp. 1729
- Dirat, O.¹ Clipson, A.² Elliott, J.M.³ Garrett, S.⁴ Jones, A.B.⁵ Reader, M.⁶ Shaw, D.⁷

35
- 10744223434
- K. C. Nicolaou, K. C. Fylaktakidou, H. Monenschein, Y. W. Li, B. Weyershausen, H. J. Mitchell, H. X. Wei, P. Guntupalli, D. Hepworth, K. Sugita, J. Am. Chem. Soc. 2003, 125, 15433.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 15433
- Nicolaou, K.C.¹ Fylaktakidou, K.C.² Monenschein, H.³ Li, Y.W.⁴ Weyershausen, B.⁵ Mitchell, H.J.⁶ Wei, H.X.⁷ Guntupalli, P.⁸ Hepworth, D.⁹ Sugita, K.¹⁰

36
- 33947293559
- D. Seyferth, R. S. Marmor, P. Hilbert, J. Org. Chem. 1971, 36, 1379.
- (1971) J. Org. Chem. , vol.36 , pp. 1379
- Seyferth, D.¹ Marmor, R.S.² Hilbert, P.³

37
- 0001174986
- J. C. Gilbert, U. Weerasooriya, J. Org. Chem. 1982, 47, 1837.
- (1982) J. Org. Chem. , vol.47 , pp. 1837
- Gilbert, J.C.¹ Weerasooriya, U.²

38
- 0034629333
- J. A. Marshall, B. A. Johns, J. Org. Chem. 2000, 65, 1501.
- (2000) J. Org. Chem. , vol.65 , pp. 1501
- Marshall, J.A.¹ Johns, B.A.²

39
- 0034800738
- D. L. Boger, S. Ichikawa, W. Zhong, J. Am. Chem. Soc. 2001, 123, 4161.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 4161
- Boger, D.L.¹ Ichikawa, S.² Zhong, W.³

40
- 0028108558
- M. F. Semmelhack, W. R. Epa, A. W. H. Cheung, Y. Gu, C. Kim, N. Zhang, W. Lew, J. Am. Chem. Soc. 1994, 116, 7455.
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 7455
- Semmelhack, M.F.¹ Epa, W.R.² Cheung, A.W.H.³ Gu, Y.⁴ Kim, C.⁵ Zhang, N.⁶ Lew, W.⁷

41
- 0348041602
- G. Pattenden, M. A. Gonzalez, P. B. Little, D. S. Millan, A. T. Plowright, J. A. Tornos, T. Ye, Org. Biomol. Chem. 2003, 1, 4173.
- (2003) Org. Biomol. Chem. , vol.1 , pp. 4173
- Pattenden, G.¹ Gonzalez, M.A.² Little, P.B.³ Millan, D.S.⁴ Plowright, A.T.⁵ Tornos, J.A.⁶ Ye, T.⁷

42
- 28844467489
- P. Dimopoulos, J. George, D. A. Tocher, S. Manaviazar, K. J. Hale, Org. Lett. 2005, 7, 5377.
- (2005) Org. Lett. , vol.7 , pp. 5377
- Dimopoulos, P.¹ George, J.² Tocher, D.A.³ Manaviazar, S.⁴ Hale, K.J.⁵

43
- 78649839366
- D. K. Mohapatra, D. P. Reddy, U. Dash, J. S. Yadav, Tetrahedron Lett. 2011, 52, 151.
- (2011) Tetrahedron Lett. , vol.52 , pp. 151
- Mohapatra, D.K.¹ Reddy, D.P.² Dash, U.³ Yadav, J.S.⁴

44
- 0034669433
- J. S. Panek, P. Liu, J. Am. Chem. Soc. 2000, 122, 11090.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 11090
- Panek, J.S.¹ Liu, P.²

45
- 0037189264
- M. Yu, B. L. Pagenkopf, J. Org. Chem. 2002, 67, 4553.
- (2002) J. Org. Chem. , vol.67 , pp. 4553
- Yu, M.¹ Pagenkopf, B.L.²

46
- 0001177017
- E. J. Corey, P. B. Hopkins, Tetrahedron Lett. 1982, 23, 4871.
- (1982) Tetrahedron Lett. , vol.23 , pp. 4871
- Corey, E.J.¹ Hopkins, P.B.²

47
- 0009606431
- K. C. Nicolaou, T. Ladduwahetty, I. M. Taffer, R. E. Zipkin, Synthesis 1986, 344.
- (1986) Synthesis , pp. 344
- Nicolaou, K.C.¹ Ladduwahetty, T.² Taffer, I.M.³ Zipkin, R.E.⁴

48
- 11444268894
- M. Ichikawa, M. Takahashi, S. Aoyagi, C. Kibayashi, J. Am. Chem. Soc. 2004, 126, 16553.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 16553
- Ichikawa, M.¹ Takahashi, M.² Aoyagi, S.³ Kibayashi, C.⁴

49
- 0001441665
- M. E. Jung, L. A. Light, Tetrahedron Lett. 1982, 23, 3851.
- (1982) Tetrahedron Lett. , vol.23 , pp. 3851
- Jung, M.E.¹ Light, L.A.²

50
- 0030607168
- P. Wipf, H. Jahn, Tetrahedron 1996, 52, 12853.
- (1996) Tetrahedron , vol.52 , pp. 12853
- Wipf, P.¹ Jahn, H.²

51
- 33947727055
- R. Chinchilla, C. Najera, Chem. Rev. 2007, 107, 874.
- (2007) Chem. Rev. , vol.107 , pp. 874
- Chinchilla, R.¹ Najera, C.²

52
- 33748617140
- Z. H. Huang, E. Negishi, Org. Lett. 2006, 8, 3675.
- (2006) Org. Lett. , vol.8 , pp. 3675
- Huang, Z.H.¹ Negishi, E.²

53
- 0002957219
- K. Miwa, T. Aoyama, T. Shioiri, Synlett 1994, 107.
- (1994) Synlett , pp. 107
- Miwa, K.¹ Aoyama, T.² Shioiri, T.³

54
- 0033538635
- A. Rodríguez, M. Nomen, B. W. Spur, J. J. Godfroid, Tetrahedron Lett. 1999, 40, 5161.
- (1999) Tetrahedron Lett. , vol.40 , pp. 5161
- Rodríguez, A.¹ Nomen, M.² Spur, B.W.³ Godfroid, J.J.⁴

55
- 80052592184
- R. Chinchilla, C. Najera, Chem. Soc. Rev. 2011, 40, 5084.
- (2011) Chem. Soc. Rev. , vol.40 , pp. 5084
- Chinchilla, R.¹ Najera, C.²

56
- 84860360013
- C. Oger, V. Bultel-Ponce, A. Guy, T. Durand, J. M. Galano, Eur. J. Org. Chem. 2012, 2621.
- (2012) Eur. J. Org. Chem. , pp. 2621
- Oger, C.¹ Bultel-Ponce, V.² Guy, A.³ Durand, T.⁴ Galano, J.M.⁵

57
- 84875128534
- C. Oger, L. Balas, T. Durand, J. M. Galano, Chem. Rev. 2013, 113, 1313.
- (2013) Chem. Rev. , vol.113 , pp. 1313
- Oger, C.¹ Balas, L.² Durand, T.³ Galano, J.M.⁴

58
- 84987453882
- W. Boland, C. Sieler, M. Feigel, Helv. Chim. Acta 1987, 70, 1025.
- (1987) Helv. Chim. Acta , vol.70 , pp. 1025
- Boland, W.¹ Sieler, C.² Feigel, M.³

59
- 82955249284
- B. W. Spur, A. R. Rodriguez, Tetrahedron Lett. 2012, 53, 86.
- (2012) Tetrahedron Lett. , vol.53 , pp. 86
- Spur, B.W.¹ Rodriguez, A.R.²

60
- 84875924026
- Y. M. A. Mohamed, T. V. Hansen, Tetrahedron 2013, 69, 3872.
- (2013) Tetrahedron , vol.69 , pp. 3872
- Mohamed, Y.M.A.¹ Hansen, T.V.²

61
- 0024381420
- D. Delorme, Y. Girard, J. Rokach, J. Org. Chem. 1989, 54, 3635.
- (1989) J. Org. Chem. , vol.54 , pp. 3635
- Delorme, D.¹ Girard, Y.² Rokach, J.³

62
- 0022645398
- M. Shinoda, K. Iseki, T. Oguri, Y. Hayasi, S. Yamada, M. Shibasaki, Tetrahedron Lett. 1986, 27, 87.
- (1986) Tetrahedron Lett. , vol.27 , pp. 87
- Shinoda, M.¹ Iseki, K.² Oguri, T.³ Hayasi, Y.⁴ Yamada, S.⁵ Shibasaki, M.⁶

63
- 0000862961
- M. Yamaguchi, Y. Nobayashi, I. Hirao, Tetrahedron 1984, 40, 4261.
- (1984) Tetrahedron , vol.40 , pp. 4261
- Yamaguchi, M.¹ Nobayashi, Y.² Hirao, I.³

64
- 0001015289
- R. Appel, Angew. Chem. 1975, 87, 863
- (1975) Angew. Chem. , vol.87 , pp. 863
- Appel, R.¹

65
- 84982373258
- Angew. Chem. Int. Ed. Engl. 1975, 14, 801.
- (1975) Angew. Chem. Int. Ed. Engl. , vol.14 , pp. 801

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.