SCOPUS 정보 검색 플랫폼

Volumn 9, Issue 10, 2011, Pages 3825-3833

Total synthesis of spiruchostatin B aided by an automated synthesizer

(9) Fuse, Shinichiro a Okada, Kumiko a Iijima, Yusuke a Munakata, Asami b MacHida, Kazuhiro c Takahashi, Takashi a Takagi, Motoki b Shin Ya, Kazuo d Doi, Takayuki e

a TOKYO INSTITUTE OF TECHNOLOGY (Japan)

b Koto ku (Japan)

c ChemGenesis Incorporated (Japan)

d NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST (Japan)

e TOHOKU UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC ALDOL REACTIONS; AUTOMATED SYNTHESIZERS; HDAC INHIBITORS; INHIBITORY ACTIVITY; NATURAL PRODUCTS; TOTAL SYNTHESIS;

AMINO ACIDS; CONDENSATION REACTIONS;

SYNTHESIS (CHEMICAL);

BIOLOGICAL PRODUCT; CYSTEINE; DEPSIPEPTIDE; HISTONE DEACETYLASE INHIBITOR; HYDROXYACID; SPIRUCHOSTATIN B;

ARTICLE; AUTOMATION; CHEMISTRY; SYNTHESIS;

AUTOMATION; BIOLOGICAL PRODUCTS; CYSTEINE; DEPSIPEPTIDES; HISTONE DEACETYLASE INHIBITORS; HYDROXY ACIDS;

EID: 79955447251 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c0ob01169j Document Type: Article

Times cited : (34)

References (61)

1
- 53249130741
- A. G. Kazantsev L. M. Thompson Nat. Rev. Drug Discovery 2008 7 854 868
- (2008) Nat. Rev. Drug Discovery , vol.7 , pp. 854-868
- Kazantsev, A.G.¹ Thompson, L.M.²

2
- 1842578986
- I. V. Gregoretti Y. M. Lee H. V. Goodson J. Mol. Biol. 2004 338 17 31
- (2004) J. Mol. Biol. , vol.338 , pp. 17-31
- Gregoretti, I.V.¹ Lee, Y.M.² Goodson, H.V.³

3
- 33748451151
- J. E. Bolden M. J. Peart R. W. Johnstone Nat. Rev. Drug Discovery 2006 5 769 784
- (2006) Nat. Rev. Drug Discovery , vol.5 , pp. 769-784
- Bolden, J.E.¹ Peart, M.J.² Johnstone, R.W.³

4
- 33845514708
- T. C. Karagiannis A. El-Osta Leukemia 2007 21 61 65
- (2007) Leukemia , vol.21 , pp. 61-65
- Karagiannis, T.C.¹ El-Osta, A.²

5
- 14644431730
- T. A. McKinsey E. N. Olson J. Clin. Invest. 2005 115 538 546
- (2005) J. Clin. Invest. , vol.115 , pp. 538-546
- McKinsey, T.A.¹ Olson, E.N.²

6
- 0035180541
- Y. Masuoka A. Nagai K. Shin-ya K. Furihata K. Nagai K. Suzuki Y. Hayakawa H. Seto Tetrahedron Lett. 2001 42 41 44
- (2001) Tetrahedron Lett. , vol.42 , pp. 41-44
- Masuoka, Y.¹ Nagai, A.² Shin-Ya, K.³ Furihata, K.⁴ Nagai, K.⁵ Suzuki, K.⁶ Hayakawa, Y.⁷ Seto, H.⁸

7
- 0028258610
- H. Ueda H. Nakajima Y. Hori T. Fujita M. Nishimura T. Goto M. Okuhara J. Antibiot. 1994 47 301 310
- (1994) J. Antibiot. , vol.47 , pp. 301-310
- Ueda, H.¹ Nakajima, H.² Hori, Y.³ Fujita, T.⁴ Nishimura, M.⁵ Goto, T.⁶ Okuhara, M.⁷

8
- 79955434968
- M. Okuhara, T. Goto, T. Fujita, Y. Hori and H. Ueda, in Jpn. Pat., 03141296, 1991
- (1991) Jpn. Pat., 03141296
- Okuhara, M.¹ Goto, T.² Fujita, T.³ Hori, Y.⁴ Ueda, H.⁵

9
- 39049135494
- K. Taori V. J. Paul H. Luesch J. Am. Chem. Soc. 2008 130 1806 1807
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 1806-1807
- Taori, K.¹ Paul, V.J.² Luesch, H.³

10
- 0036735385
- R. Furumai A. Matsuyama N. Kobashi K. H. Lee N. Nishiyama I. Nakajima A. Tanaka Y. Komatsu N. Nishino M. Yoshida S. Horinouchi Cancer Res. 2002 62 4916 4921
- (2002) Cancer Res. , vol.62 , pp. 4916-4921
- Furumai, R.¹ Matsuyama, A.² Kobashi, N.³ Lee, K.H.⁴ Nishiyama, N.⁵ Nakajima, I.⁶ Tanaka, A.⁷ Komatsu, Y.⁸ Nishino, N.⁹ Yoshida, M.¹⁰ Horinouchi, S.¹¹

11
- 0942265466
- A. Yurek-George F. Habens M. Brimmell G. Packham A. Ganesan J. Am. Chem. Soc. 2004 126 1030 1031
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 1030-1031
- Yurek-George, A.¹ Habens, F.² Brimmell, M.³ Packham, G.⁴ Ganesan, A.⁵

12
- 30544441979
- T. Doi Y. Iijima S. Y. Kazuo A. Ganesan T. Takahashi Tetrahedron Lett. 2006 47 1177 1180
- (2006) Tetrahedron Lett. , vol.47 , pp. 1177-1180
- Doi, T.¹ Iijima, Y.² Kazuo, S.Y.³ Ganesan, A.⁴ Takahashi, T.⁵

13
- 65249112206
- Y. Iijima A. Munakata K. Shin-ya A. Ganesan T. Doi T. Takahashi Tetrahedron Lett. 2009 50 2970 2972
- (2009) Tetrahedron Lett. , vol.50 , pp. 2970-2972
- Iijima, Y.¹ Munakata, A.² Shin-Ya, K.³ Ganesan, A.⁴ Doi, T.⁵ Takahashi, T.⁶

14
- 48149089435
- S. J. Crabb M. Howell H. Rogers M. Ishfaq A. Yurek-George K. Carey B. M. Pickering P. East R. Mitter S. Maeda P. W. M. Johnson P. Townsend K. Shin-Ya M. Yoshida A. Ganesan G. Packham Biochem. Pharmacol. 2008 76 463 475
- (2008) Biochem. Pharmacol. , vol.76 , pp. 463-475
- Crabb, S.J.¹ Howell, M.² Rogers, H.³ Ishfaq, M.⁴ Yurek-George, A.⁵ Carey, K.⁶ Pickering, B.M.⁷ East, P.⁸ Mitter, R.⁹ Maeda, S.¹⁰ Johnson, P.W.M.¹¹ Townsend, P.¹² Shin-Ya, K.¹³ Yoshida, M.¹⁴ Ganesan, A.¹⁵ Packham, G.¹⁶

15
- 57449102887
- T. Takizawa K. Watanabe K. Narita K. Kudo T. Oguchi H. Abe T. Katoh Heterocycles 2008 76 275 290
- (2008) Heterocycles , vol.76 , pp. 275-290
- Takizawa, T.¹ Watanabe, K.² Narita, K.³ Kudo, K.⁴ Oguchi, T.⁵ Abe, H.⁶ Katoh, T.⁷

16
- 65549147694
- N. A. Calandra Y. L. Cheng K. A. Kocak J. S. Miller Org. Lett. 2009 11 1971 1974
- (2009) Org. Lett. , vol.11 , pp. 1971-1974
- Calandra, N.A.¹ Cheng, Y.L.² Kocak, K.A.³ Miller, J.S.⁴

17
- 70350507928
- K. Narita T. Kikuchi K. Watanabe T. Takizawa T. Oguchi K. Kudo K. Matsuhara H. Abe T. Yamori M. Yoshida T. Katoh Chem.-Eur. J. 2009 15 11174 11186
- (2009) Chem.-Eur. J. , vol.15 , pp. 11174-11186
- Narita, K.¹ Kikuchi, T.² Watanabe, K.³ Takizawa, T.⁴ Oguchi, T.⁵ Kudo, K.⁶ Matsuhara, K.⁷ Abe, H.⁸ Yamori, T.⁹ Yoshida, M.¹⁰ Katoh, T.¹¹

18
- 41149138110
- T. Takizawa K. Watanabe K. Narita T. Oguchi H. Abe T. Katoh Chem. Commun. 2008 1677 1679
- (2008) Chem. Commun. , pp. 1677-1679
- Takizawa, T.¹ Watanabe, K.² Narita, K.³ Oguchi, T.⁴ Abe, H.⁵ Katoh, T.⁶

19
- 0029785860
- K. W. Li J. Wu W. N. Xing J. A. Simon J. Am. Chem. Soc. 1996 118 7237 7238
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 7237-7238
- Li, K.W.¹ Wu, J.² Xing, W.N.³ Simon, J.A.⁴

20
- 36148975704
- A. Yurek-George A. R. L. Cecil A. H. K. Mo S. J. Wen H. Rogers F. Habens S. Maeda M. Yoshida G. Packham A. Ganesan J. Med. Chem. 2007 50 5720 5726
- (2007) J. Med. Chem. , vol.50 , pp. 5720-5726
- Yurek-George, A.¹ Cecil, A.R.L.² Mo, A.H.K.³ Wen, S.J.⁴ Rogers, H.⁵ Habens, F.⁶ Maeda, S.⁷ Yoshida, M.⁸ Packham, G.⁹ Ganesan, A.¹⁰

21
- 35048856900
- E. Lech-Maranda E. Robak A. Korycka T. Robak Mini-Rev. Med. Chem. 2007 7 1062 1069
- (2007) Mini-Rev. Med. Chem. , vol.7 , pp. 1062-1069
- Lech-Maranda, E.¹ Robak, E.² Korycka, A.³ Robak, T.⁴

22
- 56249097273
- S. Di Maro R. C. Pong J. T. Hsieh J. M. Ahn J. Med. Chem. 2008 51 6639 6641
- (2008) J. Med. Chem. , vol.51 , pp. 6639-6641
- Di Maro, S.¹ Pong, R.C.² Hsieh, J.T.³ Ahn, J.M.⁴

23
- 39749098365
- T. J. Greshock D. M. Johns Y. Noguchi R. M. Williams Org. Lett. 2008 10 613 616
- (2008) Org. Lett. , vol.10 , pp. 613-616
- Greshock, T.J.¹ Johns, D.M.² Noguchi, Y.³ Williams, R.M.⁴

24
- 57449108068
- S. Wen G. Packham A. Ganesan J. Org. Chem. 2008 73 9353 9361
- (2008) J. Org. Chem. , vol.73 , pp. 9353-9361
- Wen, S.¹ Packham, G.² Ganesan, A.³

25
- 67749124307
- A. A. Bowers T. J. Greshock N. West G. Estiu S. L. Schreiber O. Wiest R. M. Williams J. E. Bradner J. Am. Chem. Soc. 2009 131 2900 2905
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 2900-2905
- Bowers, A.A.¹ Greshock, T.J.² West, N.³ Estiu, G.⁴ Schreiber, S.L.⁵ Wiest, O.⁶ Williams, R.M.⁷ Bradner, J.E.⁸

26
- 0242660847
- Y. P. Chen C. Gambs Y. Abe P. Wentworth K. D. Janda J. Org. Chem. 2003 68 8902 8905
- (2003) J. Org. Chem. , vol.68 , pp. 8902-8905
- Chen, Y.P.¹ Gambs, C.² Abe, Y.³ Wentworth, P.⁴ Janda, K.D.⁵

27
- 54149114729
- Y. Numajiri T. Takahashi M. Takagi K. Shin-Ya T. Doi Synlett 2008 2483 2486
- (2008) Synlett , pp. 2483-2486
- Numajiri, Y.¹ Takahashi, T.² Takagi, M.³ Shin-Ya, K.⁴ Doi, T.⁵

28
- 77953740289
- J. A. Souto E. Vaz I. Lepore A. C. Poppler G. Franci R. Alvarez L. Altucci A. R. de Lera J. Med. Chem. 2010 53 4654 4667
- (2010) J. Med. Chem. , vol.53 , pp. 4654-4667
- Souto, J.A.¹ Vaz, E.² Lepore, I.³ Poppler, A.C.⁴ Franci, G.⁵ Alvarez, R.⁶ Altucci, L.⁷ De Lera, A.R.⁸

29
- 77949831890
- X. Zeng B. L. Yin Z. Hu C. Z. Liao J. L. Liu S. Li Z. Li M. C. Nicklaus G. B. Zhou S. Jiang Org. Lett. 2010 12 1368 1371
- (2010) Org. Lett. , vol.12 , pp. 1368-1371
- Zeng, X.¹ Yin, B.L.² Hu, Z.³ Liao, C.Z.⁴ Liu, J.L.⁵ Li, S.⁶ Li, Z.⁷ Nicklaus, M.C.⁸ Zhou, G.B.⁹ Jiang, S.¹⁰

30
- 70449396598
- B. Wang C. J. Forsyth Synthesis 2009 2873 2880
- (2009) Synthesis , pp. 2873-2880
- Wang, B.¹ Forsyth, C.J.²

31
- 68149161259
- F. Chen A. H. Gao J. Li F. J. Nan ChemMedChem 2009 4 1269 1272
- (2009) ChemMedChem , vol.4 , pp. 1269-1272
- Chen, F.¹ Gao, A.H.² Li, J.³ Nan, F.J.⁴

32
- 50249144006
- A. Bowers N. West J. Taunton S. L. Schreiber J. E. Bradner R. M. Williams J. Am. Chem. Soc. 2008 130 11219 11222
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 11219-11222
- Bowers, A.¹ West, N.² Taunton, J.³ Schreiber, S.L.⁴ Bradner, J.E.⁵ Williams, R.M.⁶

33
- 46049100010
- Y. C. Ying K. Taori H. Kim J. Y. Hong H. Luesch J. Am. Chem. Soc. 2008 130 8455 8459
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 8455-8459
- Ying, Y.C.¹ Taori, K.² Kim, H.³ Hong, J.Y.⁴ Luesch, H.⁵

34
- 64049106355
- A. A. Bowers N. West T. L. Newkirk A. E. Troutman-Youngman S. L. Schreiber O. Wiest J. E. Bradner R. M. Williams Org. Lett. 2009 11 1301 1304
- (2009) Org. Lett. , vol.11 , pp. 1301-1304
- Bowers, A.A.¹ West, N.² Newkirk, T.L.³ Troutman-Youngman, A.E.⁴ Schreiber, S.L.⁵ Wiest, O.⁶ Bradner, J.E.⁷ Williams, R.M.⁸

35
- 52949112287
- Q. Ren L. Dai H. Zhang W. F. Tan Z. S. Xu T. Ye Synlett 2008 2379 2383
- (2008) Synlett , pp. 2379-2383
- Ren, Q.¹ Dai, L.² Zhang, H.³ Tan, W.F.⁴ Xu, Z.S.⁵ Ye, T.⁶

36
- 55949094932
- Y. C. Ying Y. X. Liu S. R. Byeon H. Kim H. Luesch J. Y. Hong Org. Lett. 2008 10 4021 4024
- (2008) Org. Lett. , vol.10 , pp. 4021-4024
- Ying, Y.C.¹ Liu, Y.X.² Byeon, S.R.³ Kim, H.⁴ Luesch, H.⁵ Hong, J.Y.⁶

37
- 55949099039
- A. K. Ghosh S. Kulkarni Org. Lett. 2008 10 3907 3909
- (2008) Org. Lett. , vol.10 , pp. 3907-3909
- Ghosh, A.K.¹ Kulkarni, S.²

38
- 52049119362
- T. Seiser F. Kamena N. Cramer Angew. Chem., Int. Ed. 2008 47 6483 6485
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 6483-6485
- Seiser, T.¹ Kamena, F.² Cramer, N.³

39
- 54049152858
- C. G. Nasveschuk D. Ungermannova X. D. Liu A. J. Phillips Org. Lett. 2008 10 3595 3598
- (2008) Org. Lett. , vol.10 , pp. 3595-3598
- Nasveschuk, C.G.¹ Ungermannova, D.² Liu, X.D.³ Phillips, A.J.⁴

40
- 70349525349
- T. L. Newkirk A. A. Bowers R. M. Williams Nat. Prod. Rep. 2009 26 1293 1320
- (2009) Nat. Prod. Rep. , vol.26 , pp. 1293-1320
- Newkirk, T.L.¹ Bowers, A.A.² Williams, R.M.³

41
- 72449142902
- Marcel Dekker Inc., New York, ChemKonzert is commercially available from ChemGenesis Inc.: 4-10-1 Nihonbashi-honcho, Chuo-ku Tokyo 103-0023, Japan. See supporting information for full picuture ChemKonzert and detailed protocol to use ChemKonzert
- D. G. Cork and T. Sugawara, Laboratory Automation in the Chemical Industries, Marcel Dekker Inc., New York, 2002
- (2002) Laboratory Automation in the Chemical Industries
- Cork, D.G.¹ Sugawara, T.²

42
- 74749099518
- K. Machida Y. Hirose S. Fuse T. Sugawara T. Takahashi Chem. Pharm. Bull. 2010 58 87 93
- (2010) Chem. Pharm. Bull. , vol.58 , pp. 87-93
- MacHida, K.¹ Hirose, Y.² Fuse, S.³ Sugawara, T.⁴ Takahashi, T.⁵

43
- 33749182636
- T. Doi S. Fuse S. Miyamoto K. Nakai D. Sasuga T. Takahashi Chem.-Asian J. 2006 1 370 383
- (2006) Chem.-Asian J. , vol.1 , pp. 370-383
- Doi, T.¹ Fuse, S.² Miyamoto, S.³ Nakai, K.⁴ Sasuga, D.⁵ Takahashi, T.⁶

44
- 72449201518
- Y. Tanaka S. Fuse H. Tanaka T. Doi T. Takahashi Org. Process Res. Dev. 2009 13 1111 1121
- (2009) Org. Process Res. Dev. , vol.13 , pp. 1111-1121
- Tanaka, Y.¹ Fuse, S.² Tanaka, H.³ Doi, T.⁴ Takahashi, T.⁵

45
- 79955372107
- T. Isobe and K. Fukuda, in Jpn. Pat., 09143173, 1995
- (1995) Jpn. Pat., 09143173
- Isobe, T.¹ Fukuda, K.²

46
- 0032505206
- C. L. Gibson K. Gillon S. Cook Tetrahedron Lett. 1998 39 6733 6736
- (1998) Tetrahedron Lett. , vol.39 , pp. 6733-6736
- Gibson, C.L.¹ Gillon, K.² Cook, S.³

47
- 0031759777
- T. Hintermann D. Seebach Helv. Chim. Acta 1998 81 2093 2126
- (1998) Helv. Chim. Acta , vol.81 , pp. 2093-2126
- Hintermann, T.¹ Seebach, D.²

48
- 0034708574
- S. Fukuzawa H. Matsuzawa S. Yoshimitsu J. Org. Chem. 2000 65 1702 1706
- (2000) J. Org. Chem. , vol.65 , pp. 1702-1706
- Fukuzawa, S.¹ Matsuzawa, H.² Yoshimitsu, S.³

49
- 0000244225
- D. A. Evans L. R. McGee Tetrahedron Lett. 1980 21 3975 3978
- (1980) Tetrahedron Lett. , vol.21 , pp. 3975-3978
- Evans, D.A.¹ McGee, L.R.²

50
- 33845557118
- D. A. Evans L. R. McGee J. Am. Chem. Soc. 1981 103 2876 2878
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2876-2878
- Evans, D.A.¹ McGee, L.R.²

51
- 0001272178
- T. Katsuki M. Yamaguchi Tetrahedron Lett. 1985 26 5807 5810
- (1985) Tetrahedron Lett. , vol.26 , pp. 5807-5810
- Katsuki, T.¹ Yamaguchi, M.²

52
- 84969808662
- D. W. Brooks L. D. L. Lu S. Masamune Angew. Chem. Int. Ed. 1979 18 72 74
- (1979) Angew. Chem. Int. Ed. , vol.18 , pp. 72-74
- Brooks, D.W.¹ Lu, L.D.L.² Masamune, S.³

53
- 0036012057
- I. Shiina R. Ibuka M. Kubota Chem. Lett. 2002 286 287
- (2002) Chem. Lett. , pp. 286-287
- Shiina, I.¹ Ibuka, R.² Kubota, M.³

54
- 0037078348
- I. Shiina M. Kubota R. Ibuka Tetrahedron Lett. 2002 43 7535 7539
- (2002) Tetrahedron Lett. , vol.43 , pp. 7535-7539
- Shiina, I.¹ Kubota, M.² Ibuka, R.³

55
- 1642334165
- I. Shiina M. Kubota H. Oshiumi M. Hashizume J. Org. Chem. 2004 69 1822 1830
- (2004) J. Org. Chem. , vol.69 , pp. 1822-1830
- Shiina, I.¹ Kubota, M.² Oshiumi, H.³ Hashizume, M.⁴

56
- 0346993611
- I. Shiina H. Oshiumi M. Hashizume Y. S. Yamai R. Ibuka Tetrahedron Lett. 2004 45 543 547
- (2004) Tetrahedron Lett. , vol.45 , pp. 543-547
- Shiina, I.¹ Oshiumi, H.² Hashizume, M.³ Yamai, Y.S.⁴ Ibuka, R.⁵

57
- 0034052416
- U. Dressel R. Renkawitz A. Baniahmad Anticancer Res. 2000 20 1017 1022
- (2000) Anticancer Res. , vol.20 , pp. 1017-1022
- Dressel, U.¹ Renkawitz, R.² Baniahmad, A.³

58
- 0024495619
- Y. Hamada Y. Kondo M. Shibata T. Shioiri J. Am. Chem. Soc. 1989 111 669 673
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 669-673
- Hamada, Y.¹ Kondo, Y.² Shibata, M.³ Shioiri, T.⁴

59
- 0026717258
- K. L. Rinehart R. Sakai V. Kishore D. W. Sullins K. M. Li J. Org. Chem. 1992 57 3007 3013
- (1992) J. Org. Chem. , vol.57 , pp. 3007-3013
- Rinehart, K.L.¹ Sakai, R.² Kishore, V.³ Sullins, D.W.⁴ Li, K.M.⁵

60
- 0003352870
- U. Schmidt M. Kroner H. Griesser Synthesis 1989 832 835
- (1989) Synthesis , pp. 832-835
- Schmidt, U.¹ Kroner, M.² Griesser, H.³

61
- 1642433417
- P. Lloydwilliams P. Monerris I. Gonzalez G. Jou E. Giralt J. Chem. Soc., Perkin Trans. 1 1994 1969 1974
- (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 1969-1974
- Lloydwilliams, P.¹ Monerris, P.² Gonzalez, I.³ Jou, G.⁴ Giralt, E.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.