SCOPUS 정보 검색 플랫폼

Organic and Biomolecular Chemistry

Volumn 9, Issue 10, 2011, Pages 3726-3732

Synthesis of the gymnodimine tetrahydrofuran core through a Ueno-Stork radical cyclization

(6) Toumieux, Sylvestre a Beniazza, Redouane a Desvergnes, Valérie a Aráoz, Rómulo b Molgó, Jordi b Landais, Yannick a

a UNIVERSITÉ DE BORDEAUX (France)

b CNRS (France)

Author keywords

[No Author keywords available]

Indexed keywords

KETONES; ORGANIC SOLVENTS;

LEWIS ACID; RADICAL CYCLIZATIONS; TETRA-HYDROFURAN; WADSWORTH-EMMONS OLEFINATION;

CYCLIZATION;

EID: 79955421165 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c1ob05240c Document Type: Article

Times cited : (12)

References (56)

1
- 0029116303
- T. Seki M. Satake L. Mackenzie H. F. Kaspar T. Yasumoto Tetrahedron Lett. 1995 36 7093 7096
- (1995) Tetrahedron Lett. , vol.36 , pp. 7093-7096
- Seki, T.¹ Satake, M.² MacKenzie, L.³ Kaspar, H.F.⁴ Yasumoto, T.⁵

2
- 0030958798
- M. Stewart J. W. Blunt M. H. G. Munro W. T. Robinson D. J. Hannah Tetrahedron Lett. 1997 38 4889 4890
- (1997) Tetrahedron Lett. , vol.38 , pp. 4889-4890
- Stewart, M.¹ Blunt, J.W.² Munro, M.H.G.³ Robinson, W.T.⁴ Hannah, D.J.⁵

3
- 0041302195
- C. O. Miles A. L. Wilkins D. J. Stirling A. L. MacKenzie J. Agric. Food Chem. 2003 51 4838 4840
- (2003) J. Agric. Food Chem. , vol.51 , pp. 4838-4840
- Miles, C.O.¹ Wilkins, A.L.² Stirling, D.J.³ MacKenzie, A.L.⁴

4
- 0034058873
- C. O. Miles A. L. Wilkins D. J. Stirling A. L. MacKenzie J. Agric. Food Chem. 2000 48 1373 1376
- (2000) J. Agric. Food Chem. , vol.48 , pp. 1373-1376
- Miles, C.O.¹ Wilkins, A.L.² Stirling, D.J.³ MacKenzie, A.L.⁴

5
- 3042706447
- R. Munday N. R. Towers L. Mackenzie; V. Beuzenberg P. T. Holland C. O. Miles Toxicon 2004 44 173 178
- (2004) Toxicon , vol.44 , pp. 173-178
- Munday, R.¹ Towers, N.R.² MacKenzie, L.³ Beuzenberg, V.⁴ Holland, P.T.⁵ Miles, C.O.⁶

6
- 54349109894
- R. Kharrat D. Servent E. Girard G. Ouanounou M. Amar R. Marrouchi E. Benoit J. Molgo J. Neurochem. 2008 107 952 963
- (2008) J. Neurochem. , vol.107 , pp. 952-963
- Kharrat, R.¹ Servent, D.² Girard, E.³ Ouanounou, G.⁴ Amar, M.⁵ Marrouchi, R.⁶ Benoit, E.⁷ Molgo, J.⁸

7
- 77950547338
- Y. Bourne Z. Radic R. Aráoz T. T. Talley E. Benoit D. Servent P. Taylor J. Molgo P. Marchot Proc. Natl. Acad. Sci. U. S. A. 2010 107 6076 6081
- (2010) Proc. Natl. Acad. Sci. U. S. A. , vol.107 , pp. 6076-6081
- Bourne, Y.¹ Radic, Z.² Aráoz, R.³ Talley, T.T.⁴ Benoit, E.⁵ Servent, D.⁶ Taylor, P.⁷ Molgo, J.⁸ Marchot, P.⁹

8
- 70349922799
- For approaches to the tetrahydrofuran core, see:
- K. Kong D. Romo C. Lee Angew. Chem., Int. Ed. 2009 48 7402 7405
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 7402-7405
- Kong, K.¹ Romo, D.² Lee, C.³

9
- 0034704624
- S. J. Yang T. Cohn D. Romo Org. Lett. 2000 2 763 766
- (2000) Org. Lett. , vol.2 , pp. 763-766
- Yang, S.J.¹ Cohn, T.² Romo, D.³

10
- 0345376253
- J. D. White G.-Q. Wang L. Quaranta Org. Lett. 2003 5 4109 4112
- (2003) Org. Lett. , vol.5 , pp. 4109-4112
- White, J.D.¹ Wang, G.-Q.² Quaranta, L.³

11
- 0001399973
- J. Ishihara J. Miyakawa T. Tsujimoto A. Murai Synlett 1997 1417 1419
- (1997) Synlett , pp. 1417-1419
- Ishihara, J.¹ Miyakawa, J.² Tsujimoto, T.³ Murai, A.⁴

12
- 0347286693
- J. D. White G.-Q. Wang L. Quaranta Org. Lett. 2003 5 4983 4986
- (2003) Org. Lett. , vol.5 , pp. 4983-4986
- White, J.D.¹ Wang, G.-Q.² Quaranta, L.³

13
- 28244472828
- For the construction of the macrocyclic core, see:
- K. Kong Z. Moussa D. Romo Org. Lett. 2005 7 5127 5130
- (2005) Org. Lett. , vol.7 , pp. 5127-5130
- Kong, K.¹ Moussa, Z.² Romo, D.³

14
- 0036186003
- T. Tsujimoto J. Ishihara M. Horie A. Murai Synlett 2002 399 402
- (2002) Synlett , pp. 399-402
- Tsujimoto, T.¹ Ishihara, J.² Horie, M.³ Murai, A.⁴

15
- 24944533470
- J. W Johannes S. Wenglowsky Y. Kishi Org. Lett. 2005 7 3997 4000
- (2005) Org. Lett. , vol.7 , pp. 3997-4000
- Johannes, J.W.¹ Wenglowsky, S.² Kishi, Y.³

16
- 33847614289
- J. D. White L. Quaranta G.-Q. Wang J. Org. Chem. 2007 72 1717 1728
- (2007) J. Org. Chem. , vol.72 , pp. 1717-1728
- White, J.D.¹ Quaranta, L.² Wang, G.-Q.³

17
- 2742528871
- Y. Ueno K. Chino M. Watanabe O. Moriya M. Okawara J. Am. Chem. Soc. 1982 104 5564 5566
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 5564-5566
- Ueno, Y.¹ Chino, K.² Watanabe, M.³ Moriya, O.⁴ Okawara, M.⁵

18
- 33845550427
- G. Stork R. Mook Jr. S. A. Biller S. D. Rychnovsky J. Am. Chem. Soc. 1983 105 3741 3742
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 3741-3742
- Stork, G.¹ Mook Jr., R.² Biller, S.A.³ Rychnovsky, S.D.⁴

19
- 0022495270
- G. Stork P. M. Sher H.-L. Chen J. Am. Chem. Soc. 1986 108 6384 6385
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 6384-6385
- Stork, G.¹ Sher, P.M.² Chen, H.-L.³

20
- 4444367074
- X. J. Salom-Roig F. Dénès P. Renaud Synthesis 2004 12 1903 1928
- (2004) Synthesis , vol.12 , pp. 1903-1928
- Salom-Roig, X.J.¹ Dénès, F.² Renaud, P.³

21
- 0001739718
- F. Villar O. Equey P. Renaud Org. Lett. 2000 2 1061 1064
- (2000) Org. Lett. , vol.2 , pp. 1061-1064
- Villar, F.¹ Equey, O.² Renaud, P.³

22
- 34250873297
- J. S. Yadav S. Joyasawal S. K. Dutta A. C. Kunwar Tetrahedron Lett. 2007 48 5335 5340
- (2007) Tetrahedron Lett. , vol.48 , pp. 5335-5340
- Yadav, J.S.¹ Joyasawal, S.² Dutta, S.K.³ Kunwar, A.C.⁴

23
- 35948963604
- J. S. Yadav L. Chetia Org. Lett. 2007 9 4587 4589
- (2007) Org. Lett. , vol.9 , pp. 4587-4589
- Yadav, J.S.¹ Chetia, L.²

24
- 38349160631
- For the synthesis of 2a, see:
- J. S. Yadav K. B. Reddy A. R. Prased H. Ur Rahman Tetrahedron 2008 64 2063 2070
- (2008) Tetrahedron , vol.64 , pp. 2063-2070
- Yadav, J.S.¹ Reddy, K.B.² Prased, A.R.³ Ur Rahman, H.⁴

25
- 53849096684
- B. Schmidt A. Biernat Chem.-Eur. J. 2008 14 6135 6141
- (2008) Chem.-Eur. J. , vol.14 , pp. 6135-6141
- Schmidt, B.¹ Biernat, A.²

26
- 0022527557
- S. D. Burke D. M. Armistead F. J. Schoenen J. M. Fevig Tetrahedron 1986 42 2787 2801
- (1986) Tetrahedron , vol.42 , pp. 2787-2801
- Burke, S.D.¹ Armistead, D.M.² Schoenen, F.J.³ Fevig, J.M.⁴

27
- 0026068775
- S. D. Burke A. D. Piscopio B. E. Marron M. A. Matulenko G. Pan Tetrahedron Lett. 1991 32 857 858
- (1991) Tetrahedron Lett. , vol.32 , pp. 857-858
- Burke, S.D.¹ Piscopio, A.D.² Marron, B.E.³ Matulenko, M.A.⁴ Pan, G.⁵

28
- 32744457110
- H. Tio T. Mizobuchi M. Tsukamoto T. Tokoroyama Tetrahedron Lett. 1986 27 6373 6376
- (1986) Tetrahedron Lett. , vol.27 , pp. 6373-6376
- Tio, H.¹ Mizobuchi, T.² Tsukamoto, M.³ Tokoroyama, T.⁴

29
- 0037039925
- For the synthesis of 2b, see:
- D. Kim J. Lee P. J. Shim J. I. Lim H. Jo S. Kim J. Org. Chem. 2002 67 764 771
- (2002) J. Org. Chem. , vol.67 , pp. 764-771
- Kim, D.¹ Lee, J.² Shim, P.J.³ Lim, J.I.⁴ Jo, H.⁵ Kim, S.⁶

30
- 33748648668
- M. G. Banwell C. T. Bui D. C. R. Hockless G. W. Simpson J. Chem. Soc., Perkin Trans. 1 1997 1261 1264
- (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 1261-1264
- Banwell, M.G.¹ Bui, C.T.² Hockless, D.C.R.³ Simpson, G.W.⁴

31
- 37249011908
- L. F. Tietze R. R. Singidi K. M. Gericke Chem.-Eur. J. 2007 13 9939 9947
- (2007) Chem.-Eur. J. , vol.13 , pp. 9939-9947
- Tietze, L.F.¹ Singidi, R.R.² Gericke, K.M.³

32
- 7044269534
- K. Chayajarus D. J. Chambers M. J. Chughtai A. J. Fairbanks Org. Lett. 2004 6 3797 3800
- (2004) Org. Lett. , vol.6 , pp. 3797-3800
- Chayajarus, K.¹ Chambers, D.J.² Chughtai, M.J.³ Fairbanks, A.J.⁴

33
- 0000501144
- N. A. Porter V. H. T. Chang D. R. Magnin B. T. Wright J. Am. Chem. Soc. 1988 110 3554 3560
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 3554-3560
- Porter, N.A.¹ Chang, V.H.T.² Magnin, D.R.³ Wright, B.T.⁴

34
- 33750075938
- W. Stalick A. Khorrami K. S. Hatton J. Org. Chem. 1986 51 3577 3581
- (1986) J. Org. Chem. , vol.51 , pp. 3577-3581
- Stalick, W.¹ Khorrami, A.² Hatton, K.S.³

35
- 0029040404
- J. C. Lopez A. M. Gomez B. Fraser-Reid J. Org. Chem. 1995 60 3871 3878
- (1995) J. Org. Chem. , vol.60 , pp. 3871-3878
- Lopez, J.C.¹ Gomez, A.M.² Fraser-Reid, B.³

36
- 0022002432
- A. L. J. Beckwith C. H. Schiesser Tetrahedron Lett. 1985 26 373 376
- (1985) Tetrahedron Lett. , vol.26 , pp. 373-376
- Beckwith, A.L.J.¹ Schiesser, C.H.²

37
- 0000020896
- A. L. J. Beckwith C. H. Schiesser Tetrahedron 1985 41 3925 3941
- (1985) Tetrahedron , vol.41 , pp. 3925-3941
- Beckwith, A.L.J.¹ Schiesser, C.H.²

38
- 0000449407
- A. L. J. Beckwith J. Zimmermann J. Org. Chem. 1991 56 5791 5796
- (1991) J. Org. Chem. , vol.56 , pp. 5791-5796
- Beckwith, A.L.J.¹ Zimmermann, J.²

39
- 33845282341
- D. C. Spellmeyer K. N. Houk J. Org. Chem. 1987 52 959 974
- (1987) J. Org. Chem. , vol.52 , pp. 959-974
- Spellmeyer, D.C.¹ Houk, K.N.²

40
- 0037419335
- F. Villar T. Kolly-Kovac O. Equey P. Renaud Chem.-Eur. J. 2003 9 1566 1577
- (2003) Chem.-Eur. J. , vol.9 , pp. 1566-1577
- Villar, F.¹ Kolly-Kovac, T.² Equey, O.³ Renaud, P.⁴

41
- 0037419006
- O. Corminboeuf P. Renaud C. H. Schiesser Chem.-Eur. J. 2003 9 1578 1584
- (2003) Chem.-Eur. J. , vol.9 , pp. 1578-1584
- Corminboeuf, O.¹ Renaud, P.² Schiesser, C.H.³

42
- 0942265474
- E. A. Colby K. C. O'Brien T. F. Jamison J. Am. Chem. Soc. 2004 126 998 999
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 998-999
- Colby, E.A.¹ O'Brien, K.C.² Jamison, T.F.³

43
- 27644579952
- J. Robertson J. W. P. Dallimore Org. Lett. 2005 7 5007 5010
- (2005) Org. Lett. , vol.7 , pp. 5007-5010
- Robertson, J.¹ Dallimore, J.W.P.²

44
- 70349770678
- 3CN mixture led to 6 in 84% yield on a multigram scale. Other conditions to cleave the O-Si bond including TBAT in THF or CsF (10 equiv.) without TBAF led to lower yields (59% and 70% respectively). See:
- J. S. Yadav B. V. Subba Reddy A. Srinivas Reddy Ch. Suresh Reddy S. Satyanarayana Raju Tetrahedron Lett. 2009 50 6631 6634
- (2009) Tetrahedron Lett. , vol.50 , pp. 6631-6634
- Yadav, J.S.¹ Subba Reddy, B.V.² Srinivas Reddy, A.³ Suresh Reddy, Ch.⁴ Satyanarayana Raju, S.⁵

45
- 64249122569
- L. Baldoni C. Marino J. Org. Chem. 2009 74 1994 2003
- (2009) J. Org. Chem. , vol.74 , pp. 1994-2003
- Baldoni, L.¹ Marino, C.²

46
- 33749030460
- V. Liautard A. E. Christina V. Desvergnes O. R. Martin J. Org. Chem. 2006 71 7337 7345
- (2006) J. Org. Chem. , vol.71 , pp. 7337-7345
- Liautard, V.¹ Christina, A.E.² Desvergnes, V.³ Martin, O.R.⁴

47
- 0000081048
- P. F. Cirillo J. S. Panek J. Org. Chem. 1990 55 6071 6073
- (1990) J. Org. Chem. , vol.55 , pp. 6071-6073
- Cirillo, P.F.¹ Panek, J.S.²

48
- 0001241704
- O. R. Martin S. P. Rao K G. Kurz H. A. El-Shenawy J. Am. Chem. Soc. 1988 110 8698 8700
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 8698-8700
- Martin, O.R.¹ Rao, S.P.² Kurz, K.G.³ El-Shenawy, H.A.⁴

49
- 0033616106
- C. H. Larsen B. H. Ridgway J. T. Shaw K. A. Woerpel J. Am. Chem. Soc. 1999 121 12208 12209
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 12208-12209
- Larsen, C.H.¹ Ridgway, B.H.² Shaw, J.T.³ Woerpel, K.A.⁴

50
- 0242414726
- D. M. Smith M. B. Tran K. A. Woerpel J. Am. Chem. Soc. 2003 125 14149 14158
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 14149-14158
- Smith, D.M.¹ Tran, M.B.² Woerpel, K.A.³

51
- 23744510729
- C. H. Larsen B. H. Ridgway J. T. Shaw D. M. Smith K. A. Woerpel J. Am. Chem. Soc. 2005 127 10879 10884
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 10879-10884
- Larsen, C.H.¹ Ridgway, B.H.² Shaw, J.T.³ Smith, D.M.⁴ Woerpel, K.A.⁵

52
- 33644528891
- 3CN, RT, 96 h) surprisingly led exclusively to recovered starting material:
- D. B. Dess J. C. Martin J. Org. Chem. 1983 48 4155 4156
- (1983) J. Org. Chem. , vol.48 , pp. 4155-4156
- Dess, D.B.¹ Martin, J.C.²

53
- 0000476716
- M. A. Blanchette W. Choy J. T. Davis A. P. Essenfeld S. Masamune W. R. Roush T. Sakai Tetrahedron Lett. 1984 25 2183 2186
- (1984) Tetrahedron Lett. , vol.25 , pp. 2183-2186
- Blanchette, M.A.¹ Choy, W.² Davis, J.T.³ Essenfeld, A.P.⁴ Masamune, S.⁵ Roush, W.R.⁶ Sakai, T.⁷

54
- 0000995951
- G. W. Kabalka T. M. Shoup N. M. Goudgaon J. Org. Chem. 1989 54 5930 5933
- (1989) J. Org. Chem. , vol.54 , pp. 5930-5933
- Kabalka, G.W.¹ Shoup, T.M.² Goudgaon, N.M.³

55
- 47849124337
- R. Aráoz M. Herdman R. Rippka A. Ledreux J. Molgó J. P. Changeux N. Tandeau de Marsac H. O. Nghiêm Toxicon 2008 52 163 174
- (2008) Toxicon , vol.52 , pp. 163-174
- Aráoz, R.¹ Herdman, M.² Rippka, R.³ Ledreux, A.⁴ Molgó, J.⁵ Changeux, J.P.⁶ Tandeau De Marsac, N.⁷ Nghiêm, H.O.⁸

56
- 29744438054
- K. W. C. Poon S. E. House G. B. Dudley Synlett 2005 20 3142 3144
- (2005) Synlett , vol.20 , pp. 3142-3144
- Poon, K.W.C.¹ House, S.E.² Dudley, G.B.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.