SCOPUS 정보 검색 플랫폼

Tetrahedron Letters

Volumn 51, Issue 52, 2010, Pages 6852-6855

Total synthesis of LL-Z1640-2 utilizing a late-stage intramolecular Nozaki-Hiyama-Kishi reaction

(4) LeClair, Christopher A a Boxer, Matthew B a Thomas, Craig J a Maloney, David J a

a NATIONAL HUMAN GENOME RESEARCH INSTITUTE (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LLZ 16402; MACROCYCLIC COMPOUND; PHOSPHOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CROSS LINKING; DEPROTECTION REACTION; DRUG SYNTHESIS; ELIMINATION REACTION; ESTERIFICATION; NOZAKI HIYAMA KISHI REACTION; SILYLATION; TEMPERATURE;

EID: 78650679421 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/j.tetlet.2010.10.092 Document Type: Article

Times cited : (27)

References (45)

1
- 33845481603
- Winssinger, N.; Barluenga, S. Chem. Commun. 2007, 22-36.
- (2007) Chem. Commun. , pp. 22-36
- Winssinger, N.¹ Barluenga, S.²

2
- 57149127991
- Hofmann, T.; Altmann, K.-H. C.R. Chimie 2008, 11, 1318-1335.
- (2008) C.R. Chimie , vol.11 , pp. 1318-1335
- Hofmann, T.¹ Altmann, K.-H.²

3
- 0019201003
- (a) Nair, M. S. R.; Carey, S. T. Tetrahedron Lett. 1980, 21, 2011-2012;
- (1980) Tetrahedron Lett. , vol.21 , pp. 2011-2012
- Nair, M.S.R.¹ Carey, S.T.²

4
- 0001107001
- (b) Nair, M. S. R.; Carey, S. T.; James, J. C. Tetrahedron 1981, 37, 2445-2449;
- (1981) Tetrahedron , vol.37 , pp. 2445-2449
- Nair, M.S.R.¹ Carey, S.T.² James, J.C.³

5
- 0027298648
- Corrected structure
- Corrected structure: (c) Agatsuma, T.; Takahashi, A.; Kabuto, C.; Nozoe, S. Chem. Pharm. Bull. 1993, 41, 373-375.
- (1993) Chem. Pharm. Bull. , vol.41 , pp. 373-375
- Agatsuma, T.¹ Takahashi, A.² Kabuto, C.³ Nozoe, S.⁴

6
- 0017859464
- Ellestad, G. A.; Lovell, F. M.; Perkinson, N. A.; Hargreaves, R. T.; McGahren, W. J. J. Org. Chem. 1978, 43, 2339-2343.
- (1978) J. Org. Chem. , vol.43 , pp. 2339-2343
- Ellestad, G.A.¹ Lovell, F.M.² Perkinson, N.A.³ Hargreaves, R.T.⁴ McGahren, W.J.⁵

7
- 0032713605
- Rawlins, P.; Mander, T.; Sadeghi, R.; Hill, S.; Gammon, G.; Foxwell, B.; Wrigley, S.; Moore, M. Int. J. Immunopharmacol. 1999, 21, 799-814.
- (1999) Int. J. Immunopharmacol. , vol.21 , pp. 799-814
- Rawlins, P.¹ Mander, T.² Sadeghi, R.³ Hill, S.⁴ Gammon, G.⁵ Foxwell, B.⁶ Wrigley, S.⁷ Moore, M.⁸

8
- 0033380609
- Zhao, A.; Lee, S. H.; Mojena, M.; Jenkins, R. G.; Patrick, D. R.; Huber, H. E.; Goetz, M. A.; Hensens, O. D.; Zink, D. L.; Vilella, D.; Dombrowski, A. W.; Lingham, R. B.; Huang, L. J. Antibiot. 1999, 52, 1086-1094.
- (1999) J. Antibiot. , vol.52 , pp. 1086-1094
- Zhao, A.¹ Lee, S.H.² Mojena, M.³ Jenkins, R.G.⁴ Patrick, D.R.⁵ Huber, H.E.⁶ Goetz, M.A.⁷ Hensens, O.D.⁸ Zink, D.L.⁹ Vilella, D.¹⁰ Dombrowski, A.W.¹¹ Lingham, R.B.¹² Huang, L.¹³

9
- 1842714965
- Sugisawa, N.; Matsuoka, M.; Okuno, T.; Igisu, H. Toxicol. Appl. Pharmacol. 2004, 196, 206-214.
- (2004) Toxicol. Appl. Pharmacol. , vol.196 , pp. 206-214
- Sugisawa, N.¹ Matsuoka, M.² Okuno, T.³ Igisu, H.⁴

10
- 0033515835
- Takehana, K.; Sato, S.; Kobayasi, T.; Maeda, T. Biochem. Biophys. Res. Commun. 1999, 257, 19-23.
- (1999) Biochem. Biophys. Res. Commun. , vol.257 , pp. 19-23
- Takehana, K.¹ Sato, S.² Kobayasi, T.³ Maeda, T.⁴

11
- 33845985927
- Ohori, M.; Kinoshita, T.; Yoshimura, S.; Varizaya, M.; Nakajima, H.; Miyake, H. Biochem. Biophys. Res. Commun. 2007, 353, 633-637.
- (2007) Biochem. Biophys. Res. Commun. , vol.353 , pp. 633-637
- Ohori, M.¹ Kinoshita, T.² Yoshimura, S.³ Varizaya, M.⁴ Nakajima, H.⁵ Miyake, H.⁶

12
- 0037903145
- Ninomiya-Tsuji, J.; Kajino, T.; Ono, K.; Ohtomo, T.; Matsumoto, M.; Shiina, M.; Mihara, M.; Tsuchiya, M.; Matsumoto, K.J. Biol. Chem. 2003, 278, 18485-18490.
- (2003) J. Biol. Chem. , vol.278 , pp. 18485-18490
- Ninomiya-Tsuji, J.¹ Kajino, T.² Ono, K.³ Ohtomo, T.⁴ Matsumoto, M.⁵ Shiina, M.⁶ Mihara, M.⁷ Tsuchiya, M.⁸ Matsumoto, K.⁹

13
- 37349049097
- Jensen, B. M.; Beaven, M. A.; Iwaki, S.; Metcalfe, D. D.; Gilfillan, A. M. J. Pharmacol. Exp. Ther. 2008, 324, 128-138.
- (2008) J. Pharmacol. Exp. Ther. , vol.324 , pp. 128-138
- Jensen, B.M.¹ Beaven, M.A.² Iwaki, S.³ Metcalfe, D.D.⁴ Gilfillan, A.M.⁵

14
- 33645233076
- Schirmer, A.; Kennedy, J.; Murli, S.; Reid, R.; Santi, D. V. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 4234-4239.
- (2006) Proc. Natl. Acad. Sci. U.S.A. , vol.103 , pp. 4234-4239
- Schirmer, A.¹ Kennedy, J.² Murli, S.³ Reid, R.⁴ Santi, D.V.⁵

15
- 51549120564
- Rastelli, G.; Rosenfeld, R.; Reid, R.; Santi, D. V. J. Struct. Biol. 2008, 164, 18-23.
- (2008) J. Struct. Biol. , vol.164 , pp. 18-23
- Rastelli, G.¹ Rosenfeld, R.² Reid, R.³ Santi, D.V.⁴

16
- 70350509085
- (a) Jogireddy, R.; Dakas, P.-Y.; Valot, G.; Barluenga, S.; Winssinger, N. Chem. Eur. J. 2009, 15, 11498-11506;
- (2009) Chem. Eur. J. , vol.15 , pp. 11498-11506
- Jogireddy, R.¹ Dakas, P.-Y.² Valot, G.³ Barluenga, S.⁴ Winssinger, N.⁵

17
- 77951686876
- (b) Jogireddy, R.; Barluenga, S.; Winssinger, N. ChemMedChem 2010, 5, 670-673.
- (2010) ChemMedChem , vol.5 , pp. 670-673
- Jogireddy, R.¹ Barluenga, S.² Winssinger, N.³

18
- 0035531879
- Tatsuta, K.; Takano, S.; Sato, T.; Nakano, S. Chem. Lett. 2001, 172-173.
- (2001) Chem. Lett. , pp. 172-173
- Tatsuta, K.¹ Takano, S.² Sato, T.³ Nakano, S.⁴

19
- 0037189130
- (a) Sellès, P.; Lett, R. Tetrahedron Lett. 2002, 43, 4621-4625;
- (2002) Tetrahedron Lett. , vol.43 , pp. 4621-4625
- Sellès, P.¹ Lett, R.²

20
- 0037189144
- (b) Selles, P.; Lett, R. Tetrahedron Lett. 2002, 43, 4627-4631.
- (2002) Tetrahedron Lett. , vol.43 , pp. 4627-4631
- Selles, P.¹ Lett, R.²

21
- 34548779745
- (a) Dakas, P.-Y.; Barluenga, S.; Totzke, F.; Zirrgiebel, U.; Winssinger, N. Angew. Chem., Int. Ed. 2007, 46, 6899-6902;
- (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 6899-6902
- Dakas, P.-Y.¹ Barluenga, S.² Totzke, F.³ Zirrgiebel, U.⁴ Winssinger, N.⁵

22
- 70350511755
- (b) Dakas, P.-Y.; Jogireddy, R.; Valot, G.; Barluenga, S.; Winssinger, N. Chem. Eur. J. 2009, 15, 11490-11497.
- (2009) Chem. Eur. J. , vol.15 , pp. 11490-11497
- Dakas, P.-Y.¹ Jogireddy, R.² Valot, G.³ Barluenga, S.⁴ Winssinger, N.⁵

23
- 34547494237
- Henry, N.; Robertson, M. N.; Marquez, R. Tetrahedron Lett. 2007, 48, 6088-6091.
- (2007) Tetrahedron Lett. , vol.48 , pp. 6088-6091
- Henry, N.¹ Robertson, M.N.² Marquez, R.³

24
- 49649094538
- Hearn, B. R.; Sundermann, K.; Cannoy, J.; Santi, D. V. ChemMedChem 2007, 2, 1598-1600.
- (2007) ChemMedChem , vol.2 , pp. 1598-1600
- Hearn, B.R.¹ Sundermann, K.² Cannoy, J.³ Santi, D.V.⁴

25
- 36749056768
- For reviews see
- For reviews see: (a) Hargaden, G.; Guiry, P. J. Adv. Synth. Catal. 2007, 349, 2407-2424;
- (2007) Adv. Synth. Catal. , vol.349 , pp. 2407-2424
- Hargaden, G.¹ Guiry, P.J.²

26
- 0037486826
- (b) Fürstner, A. Chem. Rev. 1999, 99, 991-1045;
- (1999) Chem. Rev. , vol.99 , pp. 991-1045
- Fürstner, A.¹

27
- 0032954123
- and references therein
- (c) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1-36. and references therein.
- (1999) Synthesis , pp. 1-36
- Wessjohann, L.A.¹ Scheid, G.²

28
- 0001305674
- For examples of intramolecular NHK reactions see
- For examples of intramolecular NHK reactions see: (a) Rowley, M.; Kishi, Y. Tetrahedron Lett. 1988, 29, 4909-4912;
- (1988) Tetrahedron Lett. , vol.29 , pp. 4909-4912
- Rowley, M.¹ Kishi, Y.²

29
- 0023809116
- (b) Schreiber, S. L.; Meyers, H. V. J. Am. Chem. Soc. 1988, 110, 5198-5200;
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 5198-5200
- Schreiber, S.L.¹ Meyers, H.V.²

30
- 0000431466
- (c) Rowley, M.; Kishi, Y. J. Am. Chem. Soc. 1989, 111, 2735-2737;
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 2735-2737
- Rowley, M.¹ Kishi, Y.²

31
- 0030754285
- (d) Stamos, D. P.; Sheng, X. C.; Chen, S. S.; Kishi, Y. Tetrahedron Lett. 1997, 38, 6355-6358;
- (1997) Tetrahedron Lett. , vol.38 , pp. 6355-6358
- Stamos, D.P.¹ Sheng, X.C.² Chen, S.S.³ Kishi, Y.⁴

32
- 0032485226
- (e) Oddon, G.; Uguen, D. Tetrahedron Lett. 1998, 39, 1157-1160;
- (1998) Tetrahedron Lett. , vol.39 , pp. 1157-1160
- Oddon, G.¹ Uguen, D.²

33
- 0035902267
- (f) Mi, B.; Maleczka, R. E., Jr. Org. Lett. 2001, 3, 1491-1494;
- (2001) Org. Lett. , vol.3 , pp. 1491-1494
- Mi, B.¹ Maleczka Jr., R.E.²

34
- 0037041355
- (g) Pilli, R. A.; Victor, M. M. Tetrahedron Lett. 2002, 43, 2815-2818;
- (2002) Tetrahedron Lett. , vol.43 , pp. 2815-2818
- Pilli, R.A.¹ Victor, M.M.²

35
- 38349121101
- (h) Marshall, J. A.; Eidam, P. M. Org. Lett. 2008, 10, 93-96.
- (2008) Org. Lett. , vol.10 , pp. 93-96
- Marshall, J.A.¹ Eidam, P.M.²

36
- 1342264143
- Geng, X.; Danishefsky, S. J. Org. Lett. 2004, 6, 413-416.
- (2004) Org. Lett. , vol.6 , pp. 413-416
- Geng, X.¹ Danishefsky, S.J.²

37
- 23644450183
- (a) Ferrié, L.; Capdevielle, P.; Cossy, J. Synlett 2005, 1933-1935;
- (2005) Synlett , pp. 1933-1935
- Ferrié, L.¹ Capdevielle, P.² Cossy, J.³

38
- 30344458508
- (b) BouzBouz, S.; Cossy, J. Tetrahedron Lett. 2006, 47, 901-904.
- (2006) Tetrahedron Lett. , vol.47 , pp. 901-904
- Bouzbouz, S.¹ Cossy, J.²

39
- 0038034652
- Morrill, C.; Grubbs, R. H. J. Org. Chem. 2003, 68, 6031-6034.
- (2003) J. Org. Chem. , vol.68 , pp. 6031-6034
- Morrill, C.¹ Grubbs, R.H.²

40
- 0000349575
- (a) Brown, H. C.; Hamaoka, T.; Ravindran, N. J. Am. Chem. Soc. 1973, 95, 5786-5788;
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 5786-5788
- Brown, H.C.¹ Hamaoka, T.² Ravindran, N.³

41
- 0000251973
- (b) Brown, H. C.; Hamaoka, T.; Ravindran, N. J. Am. Chem. Soc. 1973, 95, 6456-6457;
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 6456-6457
- Brown, H.C.¹ Hamaoka, T.² Ravindran, N.³

42
- 0000235747
- (c) Brown, H. C.; Subrahmanyam, C.; Hamaoka, T.; Ravindran, N.; Bowman, D. H.; Misumi, S.; Unni, M. K.; Somayaji, V.; Bhat, N. G. J. Org. Chem. 1989, 54, 6068-6075;
- (1989) J. Org. Chem. , vol.54 , pp. 6068-6075
- Brown, H.C.¹ Subrahmanyam, C.² Hamaoka, T.³ Ravindran, N.⁴ Bowman, D.H.⁵ Misumi, S.⁶ Unni, M.K.⁷ Somayaji, V.⁸ Bhat, N.G.⁹

43
- 0001143131
- (d) Brown, H. C.; Hamaoka, T.; Ravindran, N.; Subrahmanyam, C.; Somayaji, V.; Bhat, N. G. J. Org. Chem. 1989, 54, 6075-6079.
- (1989) J. Org. Chem. , vol.54 , pp. 6075-6079
- Brown, H.C.¹ Hamaoka, T.² Ravindran, N.³ Subrahmanyam, C.⁴ Somayaji, V.⁵ Bhat, N.G.⁶

44
- 33645396218
- (a) Conway, J. C.; Urch, C. J.; Quayle, p.; Xu, J. Synlett 2006, 776-780;
- (2006) Synlett , pp. 776-780
- Conway, J.C.¹ Urch, C.J.² Quayle, P.³ Xu, J.⁴

45
- 3242735104
- (b) Munoz, D. M.; Passey, S. C.; Simpson, T. J.; Willis, C. L.; Campbell, J. B.; Rosser, R. Aust. J. Org. Chem. 2004, 57, 645-649.
- (2004) Aust. J. Org. Chem. , vol.57 , pp. 645-649
- Munoz, D.M.¹ Passey, S.C.² Simpson, T.J.³ Willis, C.L.⁴ Campbell, J.B.⁵ Rosser, R.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.