SCOPUS 정보 검색 플랫폼

Volumn 63, Issue 3, 2010, Pages 438-444

Synthesis of the LeuTrp component of the celogentin family of cyclic peptides through a CH activationcross-coupling strategy

(3) Li, Barbara T Y a White, Jonathan M a Hutton, Craig A a

a UNIVERSITY OF MELBOURNE (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BIO-INSPIRED APPROACH; CYCLIC PEPTIDES; L-LEUCINE; L-TRYPTOPHAN; NATURAL PRODUCTS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

AMIDES; PALLADIUM; PEPTIDES; STEREOCHEMISTRY;

AMINO ACIDS;

EID: 77950195896 PISSN: 00049425 EISSN: None Source Type: Journal
DOI: 10.1071/CH10033 Document Type: Article

Times cited : (28)

References (24)

1
- 0029984356
- K. Hase, S. Kadota, P. Basnet,T.Takahashi,T. Namba, Biol. Pharm. Bull. 1996, 19, 567.
- (1996) Biol. Pharm. Bull. , vol.19 , pp. 567
- Hase, K.¹ Kadota, S.² Basnet, P.³ Takahashi, T.⁴ Namba, T.⁵

2
- 0031773221
- Y. Hayakawa,H. Fujii,K. Hase,Y. Ohnishi,R. Sakukawa,S. Kadota,T. Namba,I. Saiki, Biol. Pharm. Bull.,1998, 21, 1154
- (1998) Biol. Pharm. Bull. , vol.21 , pp. 1154
- Hayakawa, Y.¹ Fujii, H.² Hase, K.³ Ohnishi, Y.⁴ Sakukawa, R.⁵ Kadota, S.⁶ Namba, T.⁷ Saiki, I.⁸

3
- 0035812722
- Celogentins A-C, new antimitotic bicyclic peptides from the seeds of Celosia argentea
- DOI 10.1021/jo0103423
- J. Kobayashi, H. Suzuki, K. Shimbo, K. Takeya, H. Morita, J. Org. Chem. 2001, 66, 6626. doi:10.1021/JO0103423 (Pubitemid 32946579)
- (2001) Journal of Organic Chemistry , vol.66 , Issue.20 , pp. 6626-6633
- Kobayashi, J.¹ Suzuki, H.² Shimbo, K.³ Takeya, K.⁴ Morita, H.⁵

4
- 0041743277
- New antimitotic bicyclic peptides, celogentins D-H, and J, from the seeds of Celosia argentea
- DOI 10.1016/S0040-4020(03)00762-2
- H. Suzuki, H. Morita, S. Iwasaki, J. Kobayashi, Tetrahedron 2003, 59, 5307. doi:10.1016/S0040-4020(03)00762-2 (Pubitemid 36934484)
- (2003) Tetrahedron , vol.59 , Issue.28 , pp. 5307-5315
- Suzuki, H.¹ Morita, H.² Iwasaki, S.³ Kobayashi, J.⁴

5
- 1342281639
- Celogentin K, a new cyclic peptide from the seeds of Celosia argentea and X-ray structure of moroidin
- DOI 10.1016/j.tet.2004.01.053
- H. Suzuki, H. Morita, M. Shiro, J. Kobayashi, Tetrahedron 2004, 60, 2489. doi:10.1016/J.TET.2004.01.053 (Pubitemid 38249564)
- (2004) Tetrahedron , vol.60 , Issue.11 , pp. 2489-2495
- Suzuki, H.¹ Morita, H.² Shiro, M.³ Kobayashi, J.⁴

6
- 0022553117
- doi:10.1016/S0040-4020(01)87397-X
- C.T.-W. Leung,D. H.Williams, J. C. J. Barna, S. Foti, P.B. Oerlichs, Tetrahedron 1986, 42, 3333. doi:10.1016/S0040-4020(01)87397-X
- (1986) Tetrahedron , vol.42 , pp. 3333
- Leung, C.T.-W.¹ Williams, D.H.² Barna, J.C.J.³ Foti, S.⁴ Oerlichs, P.B.⁵

7
- 0003172615
- doi:10.1021/JO00269A028
- S. D. Kahn,P. M. Booth,J. P. Waltho,D. H. Williams,J. Org. Chem., 1989, 54, 1901, doi:10.1021/JO00269A028
- (1989) J. Org. Chem. , vol.54 , pp. 1901
- Kahn, S.D.¹ Booth, P.M.² Waltho, J.P.³ Williams, D.H.⁴

8
- 0034013609
- Stephanotic acid, a novel cyclic pentapeptide from the stern of Stephanotis floribunda
- DOI 10.1021/np990532x
- K. Yoshikawa, S. Tao, S. Arihara, J. Nat. Prod. 2000, 63, 540. doi:10.1021/NP990532X (Pubitemid 30257173)
- (2000) Journal of Natural Products , vol.63 , Issue.4 , pp. 540-542
- Yoshikawa, K.¹ Tao, S.² Arihara, S.³

9
- 33744749244
- doi:10.1021/OL060153C
- D. J. Bentley, A. M. Z. Slawin, C. J. Moody, Org. Lett. 2006, 8, 1975. doi:10.1021/OL060153C
- (2006) Org. Lett. , vol.8 , pp. 1975
- Bentley, D.J.¹ Slawin, A.M.Z.² Moody, C.J.³

10
- 10944254919
- doi:10.1039/B414996C
- D. J. Bentley, C. J. Moody, Org. Biomol. Chem., 2004, 2,3545, doi:10.1039/B414996C
- (2004) Org. Biomol. Chem. , vol.2 , pp. 3545
- Bentley, D.J.¹ Moody, C.J.²

11
- 46449103202
- doi:10.1055/S-2008-1078411
- J. Michaux, P. Retailleau, J.-M. Campagne, Synlett 2008, 1532. doi:10.1055/S-2008-1078411
- (2008) Synlett , vol.1532
- Michaux, J.¹ Retailleau, P.² Campagne, J.-M.³

12
- 76149144042
- doi:10.1021/JA909870G
- B. Ma, B. Banerjee, D. N. Litvinov, L. He, S. L. Castle, J. Am. Chem. Soc. 2010, 132, 1159. doi:10.1021/JA909870G
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 1159
- Ma, B.¹ Banerjee, B.² Litvinov, D.N.³ He, L.⁴ Castle, S.L.⁵

13
- 70349914102
- doi:10.1002/ANIE.200902425
- B. Ma, D. N. Litvinov, L. He, B. Banerjee, S. L. Castle, Angew. Chem. Int. Ed. 2009, 48, 6104. doi:10.1002/ANIE.200902425
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 6104
- Ma, B.¹ Litvinov, D.N.² He, L.³ Banerjee, B.⁴ Castle, S.L.⁵

14
- 33751175000
- doi:10.1071/CH06324
- A. K. L. Yuen, K. A. Jolliffe, C. A. Hutton, Aust. J. Chem. 2006, 59, 819. doi:10.1071/CH06324
- (2006) Aust. J. Chem. , vol.59 , pp. 819
- Yuen, A.K.L.¹ Jolliffe, K.A.² Hutton, C.A.³

15
- 77749273872
- Note added in proof: A related conjugate addition strategy to the Leu-Trp adduct, employing a tryptophan-C6 Grignard reagent and an Evans' oxazolidinone auxiliary-appended 4-methyl-2-pentenoate, was recently reported by Jia and co-workers, ultimately leading to a total synthesis of celogentin C: see, doi:10.1021/OL902944F
- Note added in proof: A related conjugate addition strategy to the Leu-Trp adduct, employing a tryptophan-C6 Grignard reagent and an Evans' oxazolidinone auxiliary-appended 4-methyl-2-pentenoate, was recently reported by Jia and co-workers, ultimately leading to a total synthesis of celogentin C: see W. Hu, F. Zhang, Z. Xu, Q. Liu, Y. Cui,Y. Jia, Org. Lett. 2010, 12, 956. doi:10.1021/OL902944F
- (2010) Org. Lett. , vol.12 , pp. 956
- Hu, W.¹ Zhang, F.² Xu, Z.³ Liu, Q.⁴ Cui, Y.⁵ Jia, Y.⁶

16
- 25444458063
- 3 C-H bonds catalyzed by palladium acetate
- DOI 10.1021/ja054549f
- V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154. doi:10.1021/JA054549F (Pubitemid 41377600)
- (2005) Journal of the American Chemical Society , vol.127 , Issue.38 , pp. 13154-13155
- Zaitsev, V.G.¹ Shabashov, D.² Daugulis, O.³

17
- 33746872900
- doi:10.1021/OL061389J
- B. V. S. Reddy, L. R. Reddy, E. J. Corey, Org. Lett. 2006, 8, 3391. doi:10.1021/OL061389J
- (2006) Org. Lett. , vol.8 , pp. 3391
- Reddy, B.V.S.¹ Reddy, L.R.² Corey, E.J.³

18
- 75749123121
- doi:10.1002/ ANIE.200905134
- Y. Feng, G. Chen, Angew. Chem. Int. Ed. 2010, 49, 958. doi:10.1002/ ANIE.200905134
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 958
- Feng, Y.¹ Chen, G.²

19
- 77950249710
- 2) was 0.0920 (all data)
- 2) was 0.0920 (all data).

20
- 0345310615
- doi:10.1246/BCSJ.48.2217
- T. Moriya, K. Hagio, N. Yoneda, Bull. Chem. Soc. Jpn. 1975, 48, 2217. doi:10.1246/BCSJ.48.2217
- (1975) Bull. Chem. Soc. Jpn. , vol.48 , pp. 2217
- Moriya, T.¹ Hagio, K.² Yoneda, N.³

21
- 53949083509
- doi:10.1016/J.BMCL.2008.09.086
- A. S. Osborne, P. Som, J. L. Metcalf, R. S. Phillips, Bioorg. Med. Chem. Lett. 2008, 18, 5750. doi:10.1016/J.BMCL.2008.09.086
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 5750
- Osborne, A.S.¹ Som, P.² Metcalf, J.L.³ Phillips, R.S.⁴

22
- 34250890071
- doi:10.1021/ OL070889P
- Y. Jia, M. Bois-Choussy, J. Zhu, Org. Lett. 2007, 9, 2401. doi:10.1021/ OL070889P
- (2007) Org. Lett. , vol.9 , pp. 2401
- Jia, Y.¹ Bois-Choussy, M.² Zhu, J.³

23
- 33947495398
- A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines
- DOI 10.1055/s-2006-958936
- E. A. Krasnokutskaya, N. I. Semenischeva, V. D. Filimonov, P. Knochel, Synthesis 2007, 81. doi:10.1055/S-2006-958936 (Pubitemid 46471264)
- (2007) Synthesis , Issue.1 , pp. 81-84
- Krasnokutskaya, E.A.¹ Semenischeva, N.I.² Filimonov, V.D.³ Knochel, P.⁴

24
- 26444455582
- Synthesis of linear tripeptides for right-hand segments of complestatin
- DOI 10.1248/cpb.53.1277
- Y.Yamada, A. Akiba, S. Arima, C. Okada, K.Yoshida, F. Itou, T. Kai, T. Satou, K. Takeda,Y. Harigaya, Chem. Pharm. Bull. 2005, 53, 1277. doi:10.1248/CPB.53.1277 (Pubitemid 41425622)
- (2005) Chemical and Pharmaceutical Bulletin , vol.53 , Issue.10 , pp. 1277-1290
- Yamada, Y.¹ Akiba, A.² Arima, S.³ Okada, C.⁴ Yoshida, K.⁵ Itou, F.⁶ Kai, T.⁷ Satou, T.⁸ Takeda, K.⁹ Harigaya, Y.¹⁰

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.