A short practical synthesis of 2′-deoxymugineic acid

Tetrahedron Letters

Volumn 46, Issue 9, 2005, Pages 1419-1421

  Singh, Satendra ^a   Crossley, George ^a   Ghosal, Saswati ^a   Lefievre, Yann ^a   Pennington, Michael W ^a  

^a Bachem Holding AG   (Switzerland)

Author keywords

2 Deoxymugineic acid; DMA; Reduced peptide bond; Reductive alkylation

Indexed keywords

2' DEOXYMUGINEIC ACID; ALDEHYDE; AZETIDINE 2 CARBOXYLIC ACID; BASE; ESTER DERIVATIVE; SIDEROPHORE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENOLYSIS; PURIFICATION; SYNTHESIS;

EID: 13444272072     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.030     Document Type: Article

References (19)

1. V. Römheld Plant Soil 130 1991 731 740
2. T. Shioiri, Y. Hamada, and F. Matsuura Tetrahedron 51 1995 3939 3958
3. Y. Ohfune, M. Tomita, and K.J. Nomoto Am. Chem. Soc. 103 1981 2409 2410
4. S. Fushiya, Y. Sato, S. Nakatsuyama, N. Kanuma, and S. Nozoe Chem. Lett. 1981 909 912
5. T. Shioiri, N. Irako, S. Sakakibara, F. Matsuura, and Y. Hamada Heterocycles 44 1997 519 530
6. F. Matsuura, Y. Hamada, and T. Shioiri Tetrahedron 50 1994 9457 9470
7. S.S. Klair, H.R. Mohan, and T. Kitahara Tetrahedron Lett. 39 1998 89 92
8. K. Miyakoshi, J. Oshita, and T. Kitahara Tetrahedron 57 2001 3355 3360
9. F. Matsuura, Y. Hamada, and T. Shioiri Tetrahedron 49 1993 8211 8222
10. S. Henrot, M. Larchevêque, and Y. Petit Synth. Commun. 16 1986 183 190
11. K. Clausen, M. Thorsen, and S.-O. Lawesson Tetrahedron Lett. 37 1981 3635 3639
12. E.C.J. Kornfeld Org. Chem. 16 1950 131 138
13. A.K. Beck, S. Blank, K. Job, D. Seebach, and Th. Sommerfeld Org. Synth. Coll. Vol. IX 1998 626 632
14. M. Mergler, F. Dick, B. Sax, C. Stähelin, and T.J. Vorherr Pept. Sci. 9 2003 518 526
15. R.F. Borch, M.D. Bernstein, and H.D.J. Durst Am. Chem. Soc. 93 1971 2897 2904
16. 6): 7.52-7.28 (m, 5H), 5.23-5.01 (m, 2H), 4.80-4.69 (m, 1H), 4.11-4.04 (m, 1H), 3.80-3.60 (m, 2H), 3.20-3.11 (m, 1H), 3.05-2.95 (m, 1H), 2.50-2.41 (m, 1H), 2.38-2.26 (m, 1H), 2.00-1.85 (m, 1H), 1.85-1.72 (m, 1H), 1.46 (s, 9H)
17. Y. Sasaki, and D.H. Coy Peptides 8 1987 119 121
18. 6): 7.52-7.31(m, 5H), 5.25 (s, 2H), 4.79-4.64 (m, 1H), 4.24-4.01 (m, 1H), 3.81-3.72 (m, 1H), 3.63-3.52 (m, 1H), 3.30-3.20 (m, 1H), 3.16-3.04 (m, 1H), 2.50-2.42 (m, 1H), 2.41-2.36 (m, 1H), 2.17-2.04 (m, 1H), 2.01-1.93 (m, 1H)
19. 6): 7.40-7.30 (m, 10H), 5.42-5.33 (m, 1H), 5.15-5.05 (m, 4H), 4.89-4.85 (m, 1H), 4.75-4.68 (m, 1H), 4.29-4.24 (m, 1H), 4.18-4.10 (m, 1H), 3.35-3.30 (m, 1H), 3.30-3.21 (m, 1H), 2.74-2.65 (m, 1H), 2.30-2.22 (m, 2H), 2.10-2.04 (m, 1H), 2.00-1.95 (m, 1H), 1.85-1.75 (m, 2H), 1.67-1.62 (m, 1H)