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Chemical Communications

Volumn , Issue 25, 2009, Pages 3738-3740

Bio-inspired polyene cyclization: Aziridinyl polyene cyclization catalyzed by InBr3

(5) Zhao, Yu Jun a Tan, Li Jun Serena a Li, Bin a Li, Si Min a Loh, Teck Peng a

a Nanyang Technological University (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AZIRIDINE DERIVATIVE; BROMINE DERIVATIVE; INDIUM; LEWIS ACID; POLYENE; POLYOLEFIN; TERPENOID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 67649855135 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b903696b Document Type: Article

Times cited : (22)

References (44)

1
- 30744474514
- -1870
- R. G. Langdon K. Bloch J. Am. Chem. Soc. 1952 74 1869 1870
- (1952) J. Am. Chem. Soc. , vol.74 , pp. 1869
- Langdon, R.G.¹ Bloch, K.²

2
- 0001651238
- -2024
- R. B. Woodward K. Bloch J. Am. Chem. Soc. 1953 75 2023 2024
- (1953) J. Am. Chem. Soc. , vol.75 , pp. 2023
- Woodward, R.B.¹ Bloch, K.²

3
- 0014023549
- -4751
- E. J. Corey W. E. Russey P. R. O. Montellano J. Am. Chem. Soc. 1966 80 4750 4751
- (1966) J. Am. Chem. Soc. , vol.80 , pp. 4750
- Corey, E.J.¹ Russey, W.E.² Montellano, P.R.O.³

4
- 0014023647
- For reviews on biomimetic polyene cyclization, see: -5938
- E. E. van Tamelen J. Willet M. Schwartz R. Nadeau J. Am. Chem. Soc. 1966 80 5937 5938
- (1966) J. Am. Chem. Soc. , vol.80 , pp. 5937
- Van Tamelen, E.E.¹ Willet, J.² Schwartz, M.³ Nadeau, R.⁴

5
- 34249801168
- J. D. Morrison, Academic Press, New York, p. 341
- P. A. Bartlett, in Asymmetric Synthesis, ed., J. D. Morrison, Academic Press, New York, 1984, vol. 3, p. 341
- (1984) Asymmetric Synthesis, Ed.
- Bartlett In, P.A.¹

6
- 30744447448
- Chiral terpenoid alkaloids bearing a 3-amino group in the A ring often have significant biological activities: -4756
- R. A. Yoder J. N. Johnston Chem. Rev. 2005 105 4730 4756
- (2005) Chem. Rev. , vol.105 , pp. 4730
- Yoder, R.A.¹ Johnston, J.N.²

7
- 19444370328
- -357
- S. Ijichi S. Tamagaki Chem. Lett. 2005 356 357
- (2005) Chem. Lett. , pp. 356
- Ijichi, S.¹ Tamagaki, S.²

8
- 0032487840
- -4657
- I. Sun H. Wang Y. Kashiwada J. Shen L. M. Cosentino C. H. Chen L. M. Yang K. H. Lee J. Med. Chem. 1998 41 4648 4657
- (1998) J. Med. Chem. , vol.41 , pp. 4648
- Sun, I.¹ Wang, H.² Kashiwada, Y.³ Shen, J.⁴ Cosentino, L.M.⁵ Chen, C.H.⁶ Yang, L.M.⁷ Lee, K.H.⁸

9
- 0033661695
- -1688
- C. Ma N. Nakamura M. Hattori Chem. Pharm. Bull. 2000 48 1681 1688
- (2000) Chem. Pharm. Bull. , vol.48 , pp. 1681
- Ma, C.¹ Nakamura, N.² Hattori, M.³

10
- 61449228382
- -464
- R. D. Goff J. S. Thorson Org. Lett. 2009 11 461 464
- (2009) Org. Lett. , vol.11 , pp. 461
- Goff, R.D.¹ Thorson, J.S.²

11
- 48249135712
- -10029
- Y. J. Zhao T. P. Loh J. Am. Chem. Soc. 2008 130 10024 10029
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 10024
- Zhao, Y.J.¹ Loh, T.P.²

12
- 52649140083
- -2145
- Y. J. Zhao T. P. Loh Org. Lett. 2008 10 2143 2145
- (2008) Org. Lett. , vol.10 , pp. 2143
- Zhao, Y.J.¹ Loh, T.P.²

13
- 33846438613
- -493
- Y. J. Zhao S. S. Chng T. P. Loh J. Am. Chem. Soc. 2007 129 492 493
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 492
- Zhao, Y.J.¹ Chng, S.S.² Loh, T.P.³

14
- 40549143408
- Recent reports on biomimetic epoxy olefin cyclization: -1436
- Y. J. Zhao T. P. Loh Chem. Commun. 2008 1434 1436
- (2008) Chem. Commun. , pp. 1434
- Zhao, Y.J.¹ Loh, T.P.²

15
- 44349127230
- -6721
- D. C. Behenna E. J. Corey J. Am. Chem. Soc. 2008 130 6720 6721
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 6720
- Behenna, D.C.¹ Corey, E.J.²

16
- 0033520737
- -10003
- A. X. Huang Z. Xiong E. J. Corey J. Am. Chem. Soc. 1999 121 9999 10003
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 9999
- Huang, A.X.¹ Xiong, Z.² Corey, E.J.³

17
- 0040340134
- -12207
- M. Bogenstätter A. Limberg L. E. Overman A. L. Tomasi J. Am. Chem. Soc. 1999 121 12206 12207
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 12206
- Bogenstätter, M.¹ Limberg, A.² Overman, L.E.³ Tomasi, A.L.⁴

18
- 41749124571
- -1355
- J. F. Zhao Y. J. Zhao T. P. Loh Chem. Commun. 2008 1353 1355
- (2008) Chem. Commun. , pp. 1353
- Zhao, J.F.¹ Zhao, Y.J.² Loh, T.P.³

19
- 27244457979
- -14921
- J. Justicia J. L. Oller-Lopez A. G. Campaña J. E. Oltra J. M. Cuerva E. Buñuel D. J. Cardenas J. Am. Chem. Soc. 2005 127 14911 14921
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 14911
- Justicia, J.¹ Oller-Lopez, J.L.² Campaña, A.G.³ Oltra, J.E.⁴ Cuerva, J.M.⁵ Buñuel, E.⁶ Cardenas, D.J.⁷

20
- 14944368513
- -718
- J. Justicia J. E. Oltra A. F. Barrero A. Guadaño A. González-Coloma J. M. Cuerva Eur. J. Org. Chem. 2005 712 718
- (2005) Eur. J. Org. Chem. , pp. 712
- Justicia, J.¹ Oltra, J.E.² Barrero, A.F.³ Guadaño, A.⁴ González- Coloma, A.⁵ Cuerva, J.M.⁶

21
- 4043089029
- -5806
- J. Justicia J. E. Oltra J. M. Cuerva J. Org. Chem. 2004 64 5803 5806
- (2004) J. Org. Chem. , vol.64 , pp. 5803
- Justicia, J.¹ Oltra, J.E.² Cuerva, J.M.³

22
- 0034598024
- -9423
- J. D. Rainier A. B. III Smith Tetrahedron Lett. 2000 41 9419 9423
- (2000) Tetrahedron Lett. , vol.41 , pp. 9419
- Rainier, J.D.¹ Iii Smith, A.B.²

23
- 37249017093
- -519
- J. D. Neighbors N. R. Mente K. D. Boss D. W. Zehnder D. F. Wiemer Tetrahedron Lett. 2008 41 516 519
- (2008) Tetrahedron Lett. , vol.41 , pp. 516
- Neighbors, J.D.¹ Mente, N.R.² Boss, K.D.³ Zehnder, D.W.⁴ Wiemer, D.F.⁵

24
- 0000677952
- -2491
- E. E. van Tamelen J. R. Hwu J. Am. Chem. Soc. 1983 105 2490 2491
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 2490
- Van Tamelen, E.E.¹ Hwu, J.R.²

25
- 77955170036
- For reviews on the selective opening of aziridines and azirines, see:, A. R. Katritzky, Elsevier Press, Amsterdam, p. 2 and 105, and references therein
- For reviews on the selective opening of aziridines and azirines, see: A. Padwa, M. C. McMills, S. C. Bergmeier, in Comprehensive Heterocyclic Chemistry III, ed., A. R. Katritzky, Elsevier Press, Amsterdam, 2008, vol. 1, p. 2 and 105, and references therein
- (2008) Comprehensive Heterocyclic Chemistry III, Ed.
- Padwa, A.¹ McMills, M.C.² Bergmeier In, S.C.³

26
- 0001673091
- For reviews on related N-acyliminium initiated polyene cyclizations, see:, B. M. Trost, Pergamon Press, Oxford
- For reviews on related N-acyliminium initiated polyene cyclizations, see: H. Hiemstra, W. N. Speckamp, in Comprehensive Organic Synthesis, ed., B. M. Trost, Pergamon Press, Oxford, 1991, vol. 2, ch. 4.5, p. 1047
- (1991) Comprehensive Organic Synthesis, Ed. , pp. 1047
- Hiemstra, H.¹ Speckamp In, W.N.²

27
- 0042801569
- -938
- J. Dijkink W. N. Speckamp Tetrahedron Lett. 1977 18 935 938
- (1977) Tetrahedron Lett. , vol.18 , pp. 935
- Dijkink, J.¹ Speckamp, W.N.²

28
- 0001307925
- No example of the catalytic epoxy olefin cyclization has been reported so far. A few of catalytic cases of variant polyene cyclization have been reported: -178
- J. Dijkink W. N. Speckamp Tetrahedron 1978 34 173 178
- (1978) Tetrahedron , vol.34 , pp. 173
- Dijkink, J.¹ Speckamp, W.N.²

29
- 34848840333
- -11881
- J. A. Feducia M. R. Gagné J. Am. Chem. Soc. 2008 129 11880 11881
- (2008) J. Am. Chem. Soc. , vol.129 , pp. 11880
- Feducia, J.A.¹ Gagné, M.R.²

30
- 51449108811
- and references therein -6014
- C. A. Mullen A. N. Campbell M. R. Gagné Angew. Chem., Int. Ed. 2008 47 6011 6014
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 6011
- Mullen, C.A.¹ Campbell, A.N.² Gagné, M.R.³

31
- 33847218271
- -903
- A. Sakakura A. Ukai K. Ishihara Nature 2007 445 900 903
- (2007) Nature , vol.445 , pp. 900
- Sakakura, A.¹ Ukai, A.² Ishihara, K.³

32
- 33845984909
- -5652
- M. Uyanik K. Ishihara H. Yamamoto Org. Lett. 2006 8 5649 5652
- (2006) Org. Lett. , vol.8 , pp. 5649
- Uyanik, M.¹ Ishihara, K.² Yamamoto, H.³

33
- 0035812385
- -8613
- D. Yang S. Gu Y. L. Yan N. Y. Zhu K. K. Cheung J. Am. Chem. Soc. 2001 123 8612 8613
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 8612
- Yang, D.¹ Gu, S.² Yan, Y.L.³ Zhu, N.Y.⁴ Cheung, K.K.⁵

34
- 0037119320
- -3017
- D. Yang S. Gu Y. L. Yan H. W. Zhao N. Y. Zhu Angew. Chem., Int. Ed. 2002 41 3014 3017
- (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3014
- Yang, D.¹ Gu, S.² Yan, Y.L.³ Zhao, H.W.⁴ Zhu, N.Y.⁵

35
- 60149098436
- -1247
- H. Yamamoto I. Sasaki Y. Hirai K. Namba H. Imagawa M. Nishizawa Angew. Chem., Int. Ed. 2009 48 1244 1247
- (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 1244
- Yamamoto, H.¹ Sasaki, I.² Hirai, Y.³ Namba, K.⁴ Imagawa, H.⁵ Nishizawa, M.⁶

36
- 84982360960
- -280
- D. Van Ende A. Krief Angew. Chem., Int. Ed. Engl. 1974 13 279 280
- (1974) Angew. Chem., Int. Ed. Engl. , vol.13 , pp. 279
- Van Ende, D.¹ Krief, A.²

37
- 0009562420
- and references therein
- L. M. Riddiford A. M. Ajami E. J. Corey H. Yamamoto J. E. Anderson J. Am. Chem. Soc. 1971 93 1815
- (1971) J. Am. Chem. Soc. , vol.93 , pp. 1815
- Riddiford, L.M.¹ Ajami, A.M.² Corey, E.J.³ Yamamoto, H.⁴ Anderson, J.E.⁵

38
- 33846595303
- -142
- T. Manaka S. I. Nagayama W. Desadee N. Yajima T. Kumamoto T. Watanabe T. Ishikawa M. Kawahata K. Yamaguchi Helv. Chim. Acta 2007 90 128 142
- (2007) Helv. Chim. Acta , vol.90 , pp. 128
- Manaka, T.¹ Nagayama, S.I.² Desadee, W.³ Yajima, N.⁴ Kumamoto, T.⁵ Watanabe, T.⁶ Ishikawa, T.⁷ Kawahata, M.⁸ Yamaguchi, K.⁹

39
- 0036068779
- -1145
- J. S. Yadav B. V. S. Reddy G. Parimala Synlett 2002 1143 1145
- (2002) Synlett , pp. 1143
- Yadav, J.S.¹ Reddy, B.V.S.² Parimala, G.³

40
- 34548030007
- -6746
- S. Peruncheralathan M. Henze C. Schneider Tetrahedron Lett. 2007 48 6743 6746
- (2007) Tetrahedron Lett. , vol.48 , pp. 6743
- Peruncheralathan, S.¹ Henze, M.² Schneider, C.³

41
- 0036280868
- -1064
- J. S. Yadav B. V. S. Reddy K. V. Rao K. S. Raj A. R. Prasad Synthesis 2002 1061 1064
- (2002) Synthesis , pp. 1061
- Yadav, J.S.¹ Reddy, B.V.S.² Rao, K.V.³ Raj, K.S.⁴ Prasad, A.R.⁵

42
- 0034841177
- Chiral azido alcohol was synthesized according to known procedures: -1418
- J. S. Yadav B. V. S. Reddy G. M. Kumar Synlett 2001 1417 1418
- (2001) Synlett , pp. 1417
- Yadav, J.S.¹ Reddy, B.V.S.² Kumar, G.M.³

43
- 0033529831
- -6096
- F. Fringuelli O. Poermatti F. Pizzo L. Vaccaro J. Org. Chem. 1999 64 6094 6096
- (1999) J. Org. Chem. , vol.64 , pp. 6094
- Fringuelli, F.¹ Poermatti, O.² Pizzo, F.³ Vaccaro, L.⁴

44
- 17444400112
- -224
- M. V. Voronkov A. V. Gontcharov R. C. Kanamarlapudi P. F. Richardson Z. M. Wang Org. Process Res. Dev. 2005 9 221 224
- (2005) Org. Process Res. Dev. , vol.9 , pp. 221
- Voronkov, M.V.¹ Gontcharov, A.V.² Kanamarlapudi, R.C.³ Richardson, P.F.⁴ Wang, Z.M.⁵

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