SCOPUS 정보 검색 플랫폼

Organic and Biomolecular Chemistry

Volumn 11, Issue 30, 2013, Pages 4957-4970

The cascade radical cyclisation approach to prenylated alkaloids: Synthesis of stephacidin A and notoamide B

(4) Simpkins, Nigel S a Pavlakos, Ilias a Weller, Michael D a Male, Louise a

a UNIVERSITY OF BIRMINGHAM (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE PROCESS; DIKETOPIPERAZINES; INDOLE ALKALOIDS; NATURAL PRODUCTS; NEW APPROACHES; RADICAL CYCLISATION; RADICAL INITIATORS; RADICAL PRECURSOR;

AMINO ACIDS; METABOLITES; NITROGEN COMPOUNDS;

ALKALOIDS;

BIOLOGICAL PRODUCT; FREE RADICAL; INDOLE ALKALOID; NOTOAMIDE B; STEPHACIDIN A;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; CYCLIZATION; FREE RADICALS; INDOLE ALKALOIDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84881099458 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c3ob40979a Document Type: Article

Times cited : (24)

References (67)

1
- 0037065301
- J. F. Qian-Cutrone S. Huang Y. Z. Shu D. Vyas C. Fairchild A. Menendez K. Krampitz R. Dalterio S. E. Klohr Q. Gao J. Am. Chem. Soc. 2002 124 14556 14557
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 14556-14557
- Qian-Cutrone, J.F.¹ Huang, S.² Shu, Y.Z.³ Vyas, D.⁴ Fairchild, C.⁵ Menendez, A.⁶ Krampitz, K.⁷ Dalterio, R.⁸ Klohr, S.E.⁹ Gao, Q.¹⁰

2
- 84881089638
- 6,291,461
- J. Qian-Cutrone, K. D. Krampitz, Y. Z. Shu and L. P. Chang, U.S. Patent 6,291,461, 2001
- (2001) U.S. Patent
- Qian-Cutrone, J.¹ Krampitz, K.D.² Shu, Y.Z.³ Chang, L.P.⁴

3
- 33846306493
- 6,066,635
- W. Fenical, P. Jensen and X. C. Cheng, U.S. Patent 6,066,635, 2000
- (2000) U.S. Patent
- Fenical, W.¹ Jensen, P.² Cheng, X.C.³

4
- 0035213907
- Y. Sugie H. Hirai T. Inagaki M. Ishiguro Y. J. Kim Y. Kojima T. Sakakibara S. Sakemi A. Sugiura Y. Suzuki L. Brennan J. Duignan L. H. Huang J. Sutcliffe N. Kojima J. Antibiot. 2001 54 911 916
- (2001) J. Antibiot. , vol.54 , pp. 911-916
- Sugie, Y.¹ Hirai, H.² Inagaki, T.³ Ishiguro, M.⁴ Kim, Y.J.⁵ Kojima, Y.⁶ Sakakibara, T.⁷ Sakemi, S.⁸ Sugiura, A.⁹ Suzuki, Y.¹⁰ Brennan, L.¹¹ Duignan, J.¹² Huang, L.H.¹³ Sutcliffe, J.¹⁴ Kojima, N.¹⁵

5
- 75749128696
- C. F. Nising Chem. Soc. Rev. 2010 39 591 599
- (2010) Chem. Soc. Rev. , vol.39 , pp. 591-599
- Nising, C.F.¹

6
- 28744435793
- C. Escolano Angew. Chem., Int. Ed. 2005 44 7670 7673
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 7670-7673
- Escolano, C.¹

7
- 17644361896
- S. B. Herzon A. G. Myers J. Am. Chem. Soc. 2005 127 5342 5344
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 5342-5344
- Herzon, S.B.¹ Myers, A.G.²

8
- 13244291528
- P. S. Baran C. A. Guerrero N. B. Ambhaikar B. D. Hafensteiner Angew. Chem., Int. Ed. 2005 44 606 609
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 606-609
- Baran, P.S.¹ Guerrero, C.A.² Ambhaikar, N.B.³ Hafensteiner, B.D.⁴

9
- 21244442370
- P. S. Baran C. A. Guerrero B. D. Hafensteiner N. B. Ambhaikar Angew. Chem., Int. Ed. 2005 44 3892 3895
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 3892-3895
- Baran, P.S.¹ Guerrero, C.A.² Hafensteiner, B.D.³ Ambhaikar, N.B.⁴

10
- 33745685914
- P. S. Baran B. D. Hafensteiner N. B. Ambhaikar C. A. Guerrero J. D. Gallagher J. Am. Chem. Soc. 2006 128 8678 8693
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 8678-8693
- Baran, P.S.¹ Hafensteiner, B.D.² Ambhaikar, N.B.³ Guerrero, C.A.⁴ Gallagher, J.D.⁵

11
- 34249089869
- T. J. Greshock A. W. Grubbs S. Tsukamoto R. M. Williams Angew. Chem., Int. Ed. 2007 46 2262 2265
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 2262-2265
- Greshock, T.J.¹ Grubbs, A.W.² Tsukamoto, S.³ Williams, R.M.⁴

12
- 34249112804
- G. D. Artman A. W. Grubbs R. M. Williams J. Am. Chem. Soc. 2007 129 6336 6342
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 6336-6342
- Artman, G.D.¹ Grubbs, A.W.² Williams, R.M.³

13
- 39049101067
- G. D. Artman A. W. Grubbs R. M. Williams J. Am. Chem. Soc. 2008 130 2114 2114
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 2114-2114
- Artman, G.D.¹ Grubbs, A.W.² Williams, R.M.³

14
- 35548993337
- T. J. Greshock R. M. Williams Org. Lett. 2007 9 4255 4258
- (2007) Org. Lett. , vol.9 , pp. 4255-4258
- Greshock, T.J.¹ Williams, R.M.²

15
- 84871557535
- T. J. Greshock R. M. Williams Org. Lett. 2012 14 6377 6378
- (2012) Org. Lett. , vol.14 , pp. 6377-6378
- Greshock, T.J.¹ Williams, R.M.²

16
- 34247540356
- J. E. Wulff S. B. Herzon R. Siegrist A. G. Myers J. Am. Chem. Soc. 2007 129 4898 4899
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 4898-4899
- Wulff, J.E.¹ Herzon, S.B.² Siegrist, R.³ Myers, A.G.⁴

17
- 36448960196
- J. E. Wulff R. Siegrist A. G. Myers J. Am. Chem. Soc. 2007 129 14444 14451
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 14444-14451
- Wulff, J.E.¹ Siegrist, R.² Myers, A.G.³

18
- 0037326264
- R. M. Williams R. J. Cox Acc. Chem. Res. 2003 36 127 139
- (2003) Acc. Chem. Res. , vol.36 , pp. 127-139
- Williams, R.M.¹ Cox, R.J.²

19
- 70350511177
- K. A. Miller R. M. Williams Chem. Soc. Rev. 2009 38 3160 3174
- (2009) Chem. Soc. Rev. , vol.38 , pp. 3160-3174
- Miller, K.A.¹ Williams, R.M.²

20
- 79958763837
- R. M. Williams J. Org. Chem. 2011 76 4221 4259
- (2011) J. Org. Chem. , vol.76 , pp. 4221-4259
- Williams, R.M.¹

21
- 33750007357
- M. Pichowicz N. S. Simpkins A. J. Blake C. Wilson Tetrahedron Lett. 2006 47 8413 8417
- (2006) Tetrahedron Lett. , vol.47 , pp. 8413-8417
- Pichowicz, M.¹ Simpkins, N.S.² Blake, A.J.³ Wilson, C.⁴

22
- 40649086596
- M. Pichowicz N. S. Simpkins A. J. Blake C. Wilson Tetrahedron 2008 64 3713 3735
- (2008) Tetrahedron , vol.64 , pp. 3713-3735
- Pichowicz, M.¹ Simpkins, N.S.² Blake, A.J.³ Wilson, C.⁴

23
- 67849087069
- F. Frebault N. S. Simpkins A. Fenwick J. Am. Chem. Soc. 2009 131 4214 4215
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 4214-4215
- Frebault, F.¹ Simpkins, N.S.² Fenwick, A.³

24
- 77955657508
- F. C. Frebault N. S. Simpkins Tetrahedron 2010 66 6585 6596
- (2010) Tetrahedron , vol.66 , pp. 6585-6596
- Frebault, F.C.¹ Simpkins, N.S.²

25
- 84856490904
- For a review, see
- N. S. Simpkins I. Pavlakos L. Male Chem. Commun. 2012 48 1958 1960
- (2012) Chem. Commun. , vol.48 , pp. 1958-1960
- Simpkins, N.S.¹ Pavlakos, I.² Male, L.³

26
- 0002563284
- For some examples, see
- C. J. Easton Chem. Rev. 1997 97 53 82
- (1997) Chem. Rev. , vol.97 , pp. 53-82
- Easton, C.J.¹

27
- 0000493583
- R. M. Williams R. W. Armstrong L. K. Maruyama J.-S. Dung O. P. Anderson J. Am. Chem. Soc. 1985 107 3246 3253
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 3246-3253
- Williams, R.M.¹ Armstrong, R.W.² Maruyama, L.K.³ Dung, J.-S.⁴ Anderson, O.P.⁵

28
- 79960963661
- E. Iwasa Y. Hamashima S. Fujishiro D. Hashizume M. Sodeoka Tetrahedron 2011 67 6587 6599
- (2011) Tetrahedron , vol.67 , pp. 6587-6599
- Iwasa, E.¹ Hamashima, Y.² Fujishiro, S.³ Hashizume, D.⁴ Sodeoka, M.⁵

29
- 0001150248
- A. J. Hutchinson Y. Kishi J. Am. Chem. Soc. 1979 101 6786 6788
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 6786-6788
- Hutchinson, A.J.¹ Kishi, Y.²

30
- 37249068440
- See for example
- L. E. Overman T. Sato Org. Lett. 2007 9 5267 5270
- (2007) Org. Lett. , vol.9 , pp. 5267-5270
- Overman, L.E.¹ Sato, T.²

31
- 0027369689
- E. Bosch M. D. Bachi J. Org. Chem. 1993 58 5581 5582
- (1993) J. Org. Chem. , vol.58 , pp. 5581-5582
- Bosch, E.¹ Bachi, M.D.²

32
- 0032560697
- See for examples
- J. Rancourt V. Gorys E. Jolicoeur Tetrahedron Lett. 1998 39 5339 5342
- (1998) Tetrahedron Lett. , vol.39 , pp. 5339-5342
- Rancourt, J.¹ Gorys, V.² Jolicoeur, E.³

33
- 81055144514
- H. Li N. Boonnak A. Padwa J. Org. Chem. 2011 76 9488 9496
- (2011) J. Org. Chem. , vol.76 , pp. 9488-9496
- Li, H.¹ Boonnak, N.² Padwa, A.³

34
- 78349287720
- C. Beemelmanns H.-U. Reissig Angew. Chem., Int. Ed. 2010 49 8021
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 8021
- Beemelmanns, C.¹ Reissig, H.-U.²

35
- 74949084706
- J. W. Tucker J. M. R. Narayanam S. W. Krabbe C. R. J. Stephenson Org. Lett. 2010 12 368 371
- (2010) Org. Lett. , vol.12 , pp. 368-371
- Tucker, J.W.¹ Narayanam, J.M.R.² Krabbe, S.W.³ Stephenson, C.R.J.⁴

36
- 67649460749
- A. Biechy S. Z. Zard Org. Lett. 2009 11 2800 2803
- (2009) Org. Lett. , vol.11 , pp. 2800-2803
- Biechy, A.¹ Zard, S.Z.²

37
- 33750039373
- J. Magolan M. A. Kerr Org. Lett. 2006 8 4561 4564
- (2006) Org. Lett. , vol.8 , pp. 4561-4564
- Magolan, J.¹ Kerr, M.A.²

38
- 27144459918
- C. V. Stevens E. V. Meenen Y. Eeckhout B. Vanderhoydonck W. Hooghe Chem. Commun. 2005 4827 4829
- (2005) Chem. Commun. , pp. 4827-4829
- Stevens, C.V.¹ Meenen, E.V.² Eeckhout, Y.³ Vanderhoydonck, B.⁴ Hooghe, W.⁵

39
- 7444263977
- A. S. Kyei K. Tchabanenko J. E. Baldwin R. M. Adlington Tetrahedron Lett. 2004 45 8931 8934
- (2004) Tetrahedron Lett. , vol.45 , pp. 8931-8934
- Kyei, A.S.¹ Tchabanenko, K.² Baldwin, J.E.³ Adlington, R.M.⁴

40
- 0037463517
- S. R. Flanagan D. C. Harrowven M. Bradley Tetrahedron Lett. 2003 44 1795 1798
- (2003) Tetrahedron Lett. , vol.44 , pp. 1795-1798
- Flanagan, S.R.¹ Harrowven, D.C.² Bradley, M.³

41
- 0035821192
- G. W. Gribble H. L. Fraser J. C. Badenock Chem. Commun. 2001 805 806
- (2001) Chem. Commun. , pp. 805-806
- Gribble, G.W.¹ Fraser, H.L.² Badenock, J.C.³

42
- 0035798119
- M.-L. Bennasar T. Roca R. Griera J. Bosch J. Org. Chem. 2001 66 7547 7551
- (2001) J. Org. Chem. , vol.66 , pp. 7547-7551
- Bennasar, M.-L.¹ Roca, T.² Griera, R.³ Bosch, J.⁴

43
- 0034707344
- L. D. Miranda R. Cruz-Almanza M. Pavón Y. Romero J. M. Muchowski Tetrahedron Lett. 2000 41 10181 10184
- (2000) Tetrahedron Lett. , vol.41 , pp. 10181-10184
- Miranda, L.D.¹ Cruz-Almanza, R.² Pavón, M.³ Romero, Y.⁴ Muchowski, J.M.⁵

44
- 0031002685
- F. E. Ziegler M. Belema J. Org. Chem. 1997 62 1083 1094
- (1997) J. Org. Chem. , vol.62 , pp. 1083-1094
- Ziegler, F.E.¹ Belema, M.²

45
- 33748733122
- C. J. Moody C. L. Norton J. Chem. Soc., Perkin Trans. 1 1997 2639 2643
- (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 2639-2643
- Moody, C.J.¹ Norton, C.L.²

46
- 1542712518
- S. Caddick K. Aboutayab K. Jenkins R. I. West J. Chem. Soc., Perkin Trans. 1 1996 675 682
- (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 675-682
- Caddick, S.¹ Aboutayab, K.² Jenkins, K.³ West, R.I.⁴

47
- 0001604061
- C.-C. Yang H.-T. Chang J.-M. Fang J. Org. Chem. 1993 58 3100 3105
- (1993) J. Org. Chem. , vol.58 , pp. 3100-3105
- Yang, C.-C.¹ Chang, H.-T.² Fang, J.-M.³

48
- 0025858374
- F. E. Ziegler L. O. Jeroncic J. Org. Chem. 1991 56 3479 3486
- (1991) J. Org. Chem. , vol.56 , pp. 3479-3486
- Ziegler, F.E.¹ Jeroncic, L.O.²

49
- 67649641698
- B. D. Hafensteiner M. Escribano E. Petricci P. S. Baran Bioorg. Med. Chem. Lett. 2009 19 3808 3810
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 3808-3810
- Hafensteiner, B.D.¹ Escribano, M.² Petricci, E.³ Baran, P.S.⁴

50
- 50249083476
- See also ref. 6
- M. P. DeMartino K. Chen P. S. Baran J. Am. Chem. Soc. 2008 130 11546 11560
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 11546-11560
- Demartino, M.P.¹ Chen, K.² Baran, P.S.³

51
- 7044286458
- The crystal structure of 16a has been reported previously by this group, see ref. 13 We thank professor Phil Baran of The Scripps Research Institute for kindly providing NMR spectra of their indoline intermediate
- B. B. Snider Chem. Rev. 1996 96 339 364
- (1996) Chem. Rev. , vol.96 , pp. 339-364
- Snider, B.B.¹

52
- 33745194136
- M. Tullberg M. Grøtli K. Luthman Tetrahedron 2006 62 7484 7491
- (2006) Tetrahedron , vol.62 , pp. 7484-7491
- Tullberg, M.¹ Grøtli, M.² Luthman, K.³

53
- 84881092609
- WO2006138347 (A2)
- B. Pedram, C. A. van Oeveren, L. Zhi, S. Zhao and Y. Shen, Int. Patent WO2006138347 (A2), 2006
- (2006) Int. Patent
- Pedram, B.¹ Van Oeveren, C.A.² Zhi, L.³ Zhao, S.⁴ Shen, Y.⁵

54
- 34249104049
- H. Kato T. Yoshida T. Tokue Y. Nojiri H. Hirota T. Ohta R. M. Williams S. Tsukamoto Angew. Chem., Int. Ed. 2007 46 2254 2256
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 2254-2256
- Kato, H.¹ Yoshida, T.² Tokue, T.³ Nojiri, Y.⁴ Hirota, H.⁵ Ohta, T.⁶ Williams, R.M.⁷ Tsukamoto, S.⁸

55
- 79961087501
- J. M. Finefield H. Kato T. J. Greshook D. H. Sherman S. Tsukamoto R. M. Williams Org. Lett. 2011 13 3802 3805
- (2011) Org. Lett. , vol.13 , pp. 3802-3805
- Finefield, J.M.¹ Kato, H.² Greshook, T.J.³ Sherman, D.H.⁴ Tsukamoto, S.⁵ Williams, R.M.⁶

56
- 84875193155
- S. W. Laws J. R. Scheerer J. Org. Chem. 2013 78 2422 2429
- (2013) J. Org. Chem. , vol.78 , pp. 2422-2429
- Laws, S.W.¹ Scheerer, J.R.²

57
- 84874038308
- J. D. Sunderhaus T. J. McAfoos J. M. Finefield H. Kato S. Li S. Tsukamoto D. H. Sherman R. M. Williams Org. Lett. 2013 15 22 25
- (2013) Org. Lett. , vol.15 , pp. 22-25
- Sunderhaus, J.D.¹ McAfoos, T.J.² Finefield, J.M.³ Kato, H.⁴ Li, S.⁵ Tsukamoto, S.⁶ Sherman, D.H.⁷ Williams, R.M.⁸

58
- 84877109615
- S. Cai Y. Luan X. Kong T. Zhu Q. Gu D. Li Org. Lett. 2013 15 2168 2171
- (2013) Org. Lett. , vol.15 , pp. 2168-2171
- Cai, S.¹ Luan, Y.² Kong, X.³ Zhu, T.⁴ Gu, Q.⁵ Li, D.⁶

59
- 84860326582
- X. Wang J. You J. B. King D. R. Powell R. H. Cichewicz J. Nat. Prod. 2012 75 707 715
- (2012) J. Nat. Prod. , vol.75 , pp. 707-715
- Wang, X.¹ You, J.² King, J.B.³ Powell, D.R.⁴ Cichewicz, R.H.⁵

60
- 84878242466
- J. Peng X.-Y. Zhang Z.-C. Tu X.-Y. Xu S.-H. Qi J. Nat. Prod. 2013 76 983 987
- (2013) J. Nat. Prod. , vol.76 , pp. 983-987
- Peng, J.¹ Zhang, X.-Y.² Tu, Z.-C.³ Xu, X.-Y.⁴ Qi, S.-H.⁵

61
- 84857257512
- S. J. Coles P. A. Gale Chem. Sci. 2012 3 683 689
- (2012) Chem. Sci. , vol.3 , pp. 683-689
- Coles, S.J.¹ Gale, P.A.²

62
- 80053551845
- Bruker AXS, Inc., Madison, Wisconsin, USA
- SMART, program for instrument control and data acquisition, Bruker AXS, Inc., Madison, Wisconsin, USA, 1997
- (1997) SMART, Program for Instrument Control and Data Acquisition

63
- 84881103554
- Bruker AXS, Inc.
- SAINTPLUS, program suite for data processing, Bruker AXS, Inc., 1997
- (1997) SAINTPLUS, Program Suite for Data Processing

64
- 84881094573
- Rigaku, 2011
- CrystalClear-SM Expert 2.0 r7, Rigaku, 2011
- CrystalClear-SM Expert 2.0 r7

65
- 34547259244
- Bruker AXS Inc., Madison, Wisconsin, USA
- G. M. Sheldrick, SADABS, 2007, Bruker AXS Inc., Madison, Wisconsin, USA
- (2007) SADABS
- Sheldrick, G.M.¹

66
- 37549039510
- G. M. Sheldrick Acta Crystallogr., Sect. A: Fundam. Crystallogr. 2008 64 112 122
- (2008) Acta Crystallogr., Sect. A: Fundam. Crystallogr. , vol.64 , pp. 112-122
- Sheldrick, G.M.¹

67
- 62649129696
- O. V. Dolomanov L. J. Bourhis R. J. Gildea J. A. K. Howard H. Puschmann J. Appl. Crystallogr. 2009 42 339
- (2009) J. Appl. Crystallogr. , vol.42 , pp. 339
- Dolomanov, O.V.¹ Bourhis, L.J.² Gildea, R.J.³ Howard, J.A.K.⁴ Puschmann, H.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.