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Angewandte Chemie - International Edition

Volumn 51, Issue 31, 2012, Pages 7786-7789

Asymmetric synthesis and biosynthetic implications of (+)-fusarisetin A

(5) Yin, Jun a Wang, Cheng a Kong, Lili a Cai, Shujun a Gao, Shuanhu a

a EAST CHINA NORMAL UNIVERSITY (China)

Author keywords

biosynthesis; natural products; peroxides; radical reactions; total synthesis

Indexed keywords

ASYMMETRIC SYNTHESIS; BIOMIMETIC OXIDATION; DIELS-ALDER; NATURAL PRODUCTS; ONE POT; RADICAL REACTIONS; TOTAL SYNTHESIS;

BIOCHEMISTRY; BIOMIMETICS; PEROXIDES; REACTION INTERMEDIATES; REACTION KINETICS;

BIOSYNTHESIS;

FUSARISETIN A; FUSED HETEROCYCLIC RINGS;

ARTICLE; CHEMISTRY; CONFORMATION; METABOLISM; STEREOISOMERISM; SYNTHESIS;

HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84864403252 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201202455 Document Type: Article

Times cited : (76)

References (65)

1
- 79955697167
- J.-H. Jang, Y. Asami, J.-P. Jang, S.-O. Kim, D. O. Moon, K.-S. Shin, D. Hashizume, M. Muroi, T. Saito, H. Oh, B. Y. Kim, H. Osada, J. S. Ahn, J. Am. Chem. Soc. 2011, 133, 6865-6867.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 6865-6867
- Jang, J.-H.¹ Asami, Y.² Jang, J.-P.³ Kim, S.-O.⁴ Moon, D.O.⁵ Shin, K.-S.⁶ Hashizume, D.⁷ Muroi, M.⁸ Saito, T.⁹ Oh, H.¹⁰ Kim, B.Y.¹¹ Osada, H.¹² Ahn, J.S.¹³

2
- 12844281685
- H. R. Burmeister, G. A. Bennett, R. F. Vesonder, C. W. Hesseltine, Antimicrob. Agents Chemother. 1974, 5, 634-639
- (1974) Antimicrob. Agents Chemother. , vol.5 , pp. 634-639
- Burmeister, H.R.¹ Bennett, G.A.² Vesonder, R.F.³ Hesseltine, C.W.⁴

3
- 0024359009
- N. J. Phillips, J. T. Goodwin, A. Fraiman, R. J. Cole, D. G. Lynn, J. Am. Chem. Soc. 1989, 111, 8223-8231; for biosynthesis, see
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8223-8231
- Phillips, N.J.¹ Goodwin, J.T.² Fraiman, A.³ Cole, R.J.⁴ Lynn, D.G.⁵

4
- 12744280771
- J. W. Sims, J. P. Fillmore, D. D. Warner, E. W. Schmidt, Chem. Commun. 2005, 186-188; for total syntheses, see
- (2005) Chem. Commun. , pp. 186-188
- Sims, J.W.¹ Fillmore, J.P.² Warner, D.D.³ Schmidt, E.W.⁴

5
- 0024359010
- E. Turos, J. E. Audia, S. J. Danishefsky, J. Am. Chem. Soc. 1989, 111, 8231-8236
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8231-8236
- Turos, E.¹ Audia, J.E.² Danishefsky, S.J.³

6
- 0034676588
- L. T. Burke, D. J. Dixon, S. V. Ley, F. Rodríguez, Org. Lett. 2000, 2, 3611-3613
- (2000) Org. Lett. , vol.2 , pp. 3611-3613
- Burke, L.T.¹ Dixon, D.J.² Ley, S.V.³ Rodríguez, F.⁴

7
- 0035953010
- Y. K. Kumiko, M. Shindo, K. Shishido, Tetrahedron Lett. 2001, 42, 2517-2519
- (2001) Tetrahedron Lett. , vol.42 , pp. 2517-2519
- Kumiko, Y.K.¹ Shindo, M.² Shishido, K.³

8
- 12844266168
- L. T. Burke, D. J. Dixon, S. V. Ley, F. Rodríguez, Org. Biomol. Chem. 2005, 3, 274-280.
- (2005) Org. Biomol. Chem. , vol.3 , pp. 274-280
- Burke, L.T.¹ Dixon, D.J.² Ley, S.V.³ Rodríguez, F.⁴

9
- 33845809486
- S. Pornpakakul, S. Roengsumran, S. Deechangvipart, A. Petsom, N. Muangsin, N. Ngamrojnavanich, N. Sriubolmas, N. Chaichit, T. Ohta, Tetrahedron Lett. 2007, 48, 651-655.
- (2007) Tetrahedron Lett. , vol.48 , pp. 651-655
- Pornpakakul, S.¹ Roengsumran, S.² Deechangvipart, S.³ Petsom, A.⁴ Muangsin, N.⁵ Ngamrojnavanich, N.⁶ Sriubolmas, N.⁷ Chaichit, N.⁸ Ohta, T.⁹

10
- 0037018483
- S. B. Singh, D. L. Zink, B. Heimbach, O. Genilloud, A. Teran, K. C. Silverman, R. B. Lingham, P. Felock, D. C. Hazuda, Org. Lett. 2002, 4, 1123-1126.
- (2002) Org. Lett. , vol.4 , pp. 1123-1126
- Singh, S.B.¹ Zink, D.L.² Heimbach, B.³ Genilloud, O.⁴ Teran, A.⁵ Silverman, K.C.⁶ Lingham, R.B.⁷ Felock, P.⁸ Hazuda, D.C.⁹

11
- 0015105006
- C. F. Meyer, J. Antibiot. 1971, 24, 558-560
- (1971) J. Antibiot. , vol.24 , pp. 558-560
- Meyer, C.F.¹

12
- 84862965195
- G. F. Crum, W. H. Devries, T. E. Eble, Arch. Microbiol. 1976, 109, 65-74
- (1976) Arch. Microbiol. , vol.109 , pp. 65-74
- Crum, G.F.¹ Devries, W.H.² Eble, T.E.³

13
- 73349123817
- J. C. Carlson, S. Li, D. A. Burr, D. H. Sherman, J. Nat. Prod. 2009, 72, 2076-2079.
- (2009) J. Nat. Prod. , vol.72 , pp. 2076-2079
- Carlson, J.C.¹ Li, S.² Burr, D.A.³ Sherman, D.H.⁴

14
- 0001246453
- For a review of tetramic-acid-type natural products, see:, B. J. L. Royles, Chem. Rev. 1995, 95, 1981-2001.
- (1995) Chem. Rev. , vol.95 , pp. 1981-2001
- Royles, B.J.L.¹

15
- 84855979777
- J. Deng, B. Zhu, Z.-Y. Lu, H.-X. Yu, A. Li, J. Am. Chem. Soc. 2012, 134, 920-923.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 920-923
- Deng, J.¹ Zhu, B.² Lu, Z.-Y.³ Yu, H.-X.⁴ Li, A.⁵

16
- 84863381189
- J. Xu, E. J. E. Caro-Diaz, L. Trzoss, E. A. Theodorakis, J. Am. Chem. Soc. 2012, 134, 5072-5075.
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 5072-5075
- Xu, J.¹ Caro-Diaz, E.J.E.² Trzoss, L.³ Theodorakis, E.A.⁴

17
- 0001398901
- For a review of radical cascade cyclizations, see:, A. J. J. McCarroll, C. Walton, Angew. Chem. 2001, 113, 2282-2307
- (2001) Angew. Chem. , vol.113 , pp. 2282-2307
- McCarroll, A.J.J.¹ Walton, C.²

18
- 0035907919
- Angew. Chem. Int. Ed. 2001, 40, 2224-2248.
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2224-2248

19
- 37049076286
- D. Craig, Chem. Soc. Rev. 1987, 16, 187-238
- (1987) Chem. Soc. Rev. , vol.16 , pp. 187-238
- Craig, D.¹

20
- 0037901375
- K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. Vassilikogiannakis, Angew. Chem. 2002, 114, 1742-1773
- (2002) Angew. Chem. , vol.114 , pp. 1742-1773
- Nicolaou, K.C.¹ Snyder, S.A.² Montagnon, T.³ Vassilikogiannakis, G.⁴

21
- 0036259981
- Angew. Chem. Int. Ed. 2002, 41, 1668-1698; for a review of IMDA in total synthesis, see
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1668-1698

22
- 30744456747
- K. Takao, R. Munakata, K. Tadano, Chem. Rev. 2005, 105, 4779-4807.
- (2005) Chem. Rev. , vol.105 , pp. 4779-4807
- Takao, K.¹ Munakata, R.² Tadano, K.³

23
- 58249104242
- Y. Nishikawa, M. Kitajima, N. Kogure, H. Takayama, Tetrahedron 2009, 65, 1608-1617.
- (2009) Tetrahedron , vol.65 , pp. 1608-1617
- Nishikawa, Y.¹ Kitajima, M.² Kogure, N.³ Takayama, H.⁴

24
- 7044286458
- B. B. Snider, Chem. Rev. 1996, 96, 339-364
- (1996) Chem. Rev. , vol.96 , pp. 339-364
- Snider, B.B.¹

25
- 0000768134
- 3-based radical reactions, see
- (1997) Org. React. , vol.49 , pp. 427-520
- Melikyan, G.G.¹

26
- 70449725405
- 3-promoted radical reactions, see
- (2009) Tetrahedron , vol.65 , pp. 10738-10744
- Snider, B.B.¹

27
- 0001050644
- B. B. Snider, J. J. Patricia, S. A. Kates, J. Org. Chem. 1988, 53, 2137-2143
- (1988) J. Org. Chem. , vol.53 , pp. 2137-2143
- Snider, B.B.¹ Patricia, J.J.² Kates, S.A.³

28
- 0001556501
- D. P. Curran, T. M. Morgan, C. E. Schwartz, B. B. Snider, M. A. Dombroski, J. Am. Chem. Soc. 1991, 113, 6607-6617
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 6607-6617
- Curran, D.P.¹ Morgan, T.M.² Schwartz, C.E.³ Snider, B.B.⁴ Dombroski, M.A.⁵

29
- 0001618833
- B. B. Snider, B. A. McCarthy, J. Org. Chem. 1993, 58, 6217-6223
- (1993) J. Org. Chem. , vol.58 , pp. 6217-6223
- Snider, B.B.¹ McCarthy, B.A.²

30
- 0000899183
- B. B. Snider, J. E. Merritt, M. A. Domboski, B. O. Buckman, J. Org. Chem. 1991, 56, 5544-5553; for studies of the mechanism of oxidation of radicals by copper(II), see
- (1991) J. Org. Chem. , vol.56 , pp. 5544-5553
- Snider, B.B.¹ Merritt, J.E.² Domboski, M.A.³ Buckman, B.O.⁴

31
- 0004032955
- Wiley, New York, 1973, chap. 11
- J. K. Kochi, in Free Radicals, Vol. 1 (Ed.:, J. K. Kochi,), Wiley, New York, 1973, chap. 11
- (1973) Free Radicals , vol.1
- Kochi, J.K.¹

32
- 0000247876
- J. K. Kochi, Acc. Chem. Res. 1974, 7, 351-360
- (1974) Acc. Chem. Res. , vol.7 , pp. 351-360
- Kochi, J.K.¹

33
- 0005272054
- B. B. Snider, T. Kwon, J. Org. Chem. 1990, 55, 1965-1968.
- (1990) J. Org. Chem. , vol.55 , pp. 1965-1968
- Snider, B.B.¹ Kwon, T.²

34
- 0001367691
- E. J. Corey, M.-C. Kang, J. Am. Chem. Soc. 1984, 106, 5384-5385.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 5384-5385
- Corey, E.J.¹ Kang, M.-C.²

35
- 0001356623
- A. B. Ernst, W. E. Fristad, Tetrahedron Lett. 1985, 26, 3761-3764.
- (1985) Tetrahedron Lett. , vol.26 , pp. 3761-3764
- Ernst, A.B.¹ Fristad, W.E.²

36
- 0027293888
- B. B. Snider, Q. Zhang, J. Org. Chem. 1993, 58, 3185-3187
- (1993) J. Org. Chem. , vol.58 , pp. 3185-3187
- Snider, B.B.¹ Zhang, Q.²

37
- 0027992605
- N. H. Vo, B. B. Snider, J. Org. Chem. 1994, 59, 5419-5423
- (1994) J. Org. Chem. , vol.59 , pp. 5419-5423
- Vo, N.H.¹ Snider, B.B.²

38
- 0032544313
- D. Yang, X.-Y. Ye, M. Xu, K.-W. Pang, N. Zou, R. M. Letcher, J. Org. Chem. 1998, 63, 6446-6447
- (1998) J. Org. Chem. , vol.63 , pp. 6446-6447
- Yang, D.¹ Ye, X.-Y.² Xu, M.³ Pang, K.-W.⁴ Zou, N.⁵ Letcher, R.M.⁶

39
- 0033575111
- D. Yang, X.-Y. Ye, S. Gu, M. Xu, J. Am. Chem. Soc. 1999, 121, 5579-5580
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5579-5580
- Yang, D.¹ Ye, X.-Y.² Gu, S.³ Xu, M.⁴

40
- 0034050738
- D. Yang, X.-Y. Ye, M. Xu, K.-W. Pang, K.-K. Cheung, J. Am. Chem. Soc. 2000, 122, 1658-1663
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 1658-1663
- Yang, D.¹ Ye, X.-Y.² Xu, M.³ Pang, K.-W.⁴ Cheung, K.-K.⁵

41
- 34548614055
- X. Tan, C. Chen, Angew. Chem. 2006, 118, 4451-4454
- (2006) Angew. Chem. , vol.118 , pp. 4451-4454
- Tan, X.¹ Chen, C.²

42
- 33746288746
- Angew. Chem. Int. Ed. 2006, 45, 4345-4348
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 4345-4348

43
- 78649840466
- Z. Ma, J. Lu, X. Wang, C. Chen, Chem. Commun. 2011, 47, 427-429
- (2011) Chem. Commun. , vol.47 , pp. 427-429
- Ma, Z.¹ Lu, J.² Wang, X.³ Chen, C.⁴

44
- 80053302917
- X. Wang, Z. Ma, J. Lu, X. Tan, C. Chen, J. Am. Chem. Soc. 2011, 133, 15350-15353.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 15350-15353
- Wang, X.¹ Ma, Z.² Lu, J.³ Tan, X.⁴ Chen, C.⁵

45
- 70349914336
- 2, see
- (2006) Top. Heterocycl. Chem. , vol.6 , pp. 39-76
- Nishino, H.¹

46
- 0025248639
- J. Yoshida, S. Nakatani, S. Isoe, Tetrahedron Lett. 1990, 31, 2425-2428
- (1990) Tetrahedron Lett. , vol.31 , pp. 2425-2428
- Yoshida, J.¹ Nakatani, S.² Isoe, S.³

47
- 0000367098
- H. Nishino, S. Tategami, T. Yamada, J. D. Korp, K. Kurosawa, Bull. Chem. Soc. Jpn. 1991, 64, 1800-1809
- (1991) Bull. Chem. Soc. Jpn. , vol.64 , pp. 1800-1809
- Nishino, H.¹ Tategami, S.² Yamada, T.³ Korp, J.D.⁴ Kurosawa, K.⁵

48
- 0027317235
- C. Qian, J. D. Korp, J. Org. Chem. 1993, 58, 4448-4451
- (1993) J. Org. Chem. , vol.58 , pp. 4448-4451
- Qian, C.¹ Korp, J.D.²

49
- 0032503997
- A. Boto, R. Hernández, S. M. Velázquez, E. Suáre, J. Org. Chem. 1998, 63, 4697-4705
- (1998) J. Org. Chem. , vol.63 , pp. 4697-4705
- Boto, A.¹ Hernández, R.² Velázquez, S.M.³ Suáre, E.⁴

50
- 0034619901
- T. Iwahama, S. Sakaguchi, Y. Ishii, Chem. Commun. 2000, 2317-2318
- (2000) Chem. Commun. , pp. 2317-2318
- Iwahama, T.¹ Sakaguchi, S.² Ishii, Y.³

51
- 0037039898
- K. Hirase, T. Iwahama, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2002, 67, 970-973.
- (2002) J. Org. Chem. , vol.67 , pp. 970-973
- Hirase, K.¹ Iwahama, T.² Sakaguchi, S.³ Ishii, Y.⁴

52
- 84952096388
- S. K. Taylor, Org. Prep. Proced. Int. 1992, 24, 245-284
- (1992) Org. Prep. Proced. Int. , vol.24 , pp. 245-284
- Taylor, S.K.¹

53
- 0033866183
- U. Scholz, E. Winterfeldt, Nat. Prod. Rep. 2000, 17, 349-366
- (2000) Nat. Prod. Rep. , vol.17 , pp. 349-366
- Scholz, U.¹ Winterfeldt, E.²

54
- 30744447448
- R. A. Yoder, J. N. Johnston, Chem. Rev. 2005, 105, 4730-4756
- (2005) Chem. Rev. , vol.105 , pp. 4730-4756
- Yoder, R.A.¹ Johnston, J.N.²

55
- 30744456247
- C. M. Beaudry, J. P. Malerich, D. Trauner, Chem. Rev. 2005, 105, 4757-4778
- (2005) Chem. Rev. , vol.105 , pp. 4757-4778
- Beaudry, C.M.¹ Malerich, J.P.² Trauner, D.³

56
- 33750574345
- E. Brunoldi, M. Luparia, A. Porta, G. Zanoni, G. Vidari, Curr. Org. Chem. 2006, 10, 2259-2282
- (2006) Curr. Org. Chem. , vol.10 , pp. 2259-2282
- Brunoldi, E.¹ Luparia, M.² Porta, A.³ Zanoni, G.⁴ Vidari, G.⁵

57
- 41749104435
- P. G. Bulger, S. K. Bagal, R. Marquez, Nat. Prod. Rep. 2008, 25, 254-297
- (2008) Nat. Prod. Rep. , vol.25 , pp. 254-297
- Bulger, P.G.¹ Bagal, S.K.² Marquez, R.³

58
- 81355123306
- M. Rrazzak, J. K. De Brabander, Nat. Chem. Biol. 2011, 7, 865-875.
- (2011) Nat. Chem. Biol. , vol.7 , pp. 865-875
- Rrazzak, M.¹ De Brabander, J.K.²

59
- 0001566484
- J. M. Liu, M. Y. Ni, J. F. Fen, Y. Y. Tu, Z. H. Wu, Y. L. Wu, W. S. Zhou, Huaxue Xuebao 1979, 37, 129-141
- (1979) Huaxue Xuebao , vol.37 , pp. 129-141
- Liu, J.M.¹ Ni, M.Y.² Fen, J.F.³ Tu, Y.Y.⁴ Wu, Z.H.⁵ Wu, Y.L.⁶ Zhou, W.S.⁷

60
- 0021168184
- D. L. Klayman, A. J. Lin, N. Acton, J. P. Scovill, J. M. Hoch, W. K. Milhous, A. D. Theoharides, A. S. Dobek, J. Nat. Prod. 1984, 47, 715-717
- (1984) J. Nat. Prod. , vol.47 , pp. 715-717
- Klayman, D.L.¹ Lin, A.J.² Acton, N.³ Scovill, J.P.⁴ Hoch, J.M.⁵ Milhous, W.K.⁶ Theoharides, A.D.⁷ Dobek, A.S.⁸

61
- 0021948029
- D. L. Klayman, Science 1985, 228, 1049-1055
- (1985) Science , vol.228 , pp. 1049-1055
- Klayman, D.L.¹

62
- 0001815264
- R. K. Haynes, S. C. Vonwiller, Acc. Chem. Res. 1997, 30, 73-79
- (1997) Acc. Chem. Res. , vol.30 , pp. 73-79
- Haynes, R.K.¹ Vonwiller, S.C.²

63
- 0030627218
- H. Ziffer, R. J. Highet, D. L. Klayman, Prog. Chem. Org. Nat. Prod. 1997, 72, 121-214
- (1997) Prog. Chem. Org. Nat. Prod. , vol.72 , pp. 121-214
- Ziffer, H.¹ Highet, R.J.² Klayman, D.L.³

64
- 0002776039
- and references therein
- Y. Li, Y.-L. Wu, Médcine Tropicale 1998, 58 (Suppl. 3), 9- 12, and references therein.
- (1998) Médcine Tropicale , vol.58 , Issue.SUPPL. 3 , pp. 9-12
- Li, Y.¹ Wu, Y.-L.²

65
- 0023933802
- For the isolation of yingzhaosu, see:, L. Zhang, W.-S. Zhou, X. X. Xu, J. Chem. Soc. Chem. Commun. 1988, 523-524.
- (1988) J. Chem. Soc. Chem. Commun. , pp. 523-524
- Zhang, L.¹ Zhou, W.-S.² Xu, X.X.³

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