A novel synthetic approach towards phytosiderophores: Expeditious synthesis of nicotianamine and 2'-deoxymugineic acid

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 89-92

  Klair, Sukhbinder S ^a   Mohan, Hindupur R ^a   Kitahara, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXYMUGINEIC ACID; NICOTIANAMINE; SIDEROPHORE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DESULFURIZATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0031973921     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10496-8     Document Type: Article

References (19)

1. Klair S., Hider R.C., Adams M.Z., Leigh R.A. J. Plant Nutr. 19:1996;1295-1307.
2. Shioiri T., Irako N., Sakakibara S., Matsuura F., Hamada Y. Heterocycles. 44:1997;519-530.
3. Shioiri T., Hamada Y., Matsuura F. Tetrahedron. 51:1995;3939-3958. and refs. cited therein.
4. a) Kornet, M.J.; Thio, P.A.; Tan, S.I. J.Org.Chem. 1968, 33, 3637-3639.
5. b) Russ, P.L.; Caress, E.A. J.Org.Chem. 1976, 41, 149-151.
6. c) Roeske, R.W.; Weitl, F.L.; Prasad, K.U.; Thompson, R.M. J.Org.Chem. 1976, 41, 1260-1261.
7. Dener J.M., Hart D.J., Ramesh S. J.Org.Chem. 53:1988;6022-6030.
8. a) Kristensen, I.; Larsen, P.O. Phytochemistry 1974, 13, 2791-2798.
9. b) Ripperger, H.; Schreiber, K. Heterocycles 1982, 17, 447-461.
10. c) Fushiya, S.; Nakatsuyama, S.; Sato, Y.; Nozoe, S. Heterocycles 1981, 15, 819-822.
11. Matsuura F., Hamada Y., Shioiri T. Tetrahedron. 49:1993;8211-8222.
12. Dourtoglou, V.; Gross, B. Synthesis 1984, 572-574.
13. Ramsamy, K.; Olsen, R.K.; Emery, T. Synthesis 1982, 42-43.
14. Clausen K., Thorsen M., Lawesson S.-O. Tetrahedron. 37:1981;3635-3639.
15. Gregory, H.; Morley, J.S.; Smith, J.M.; Smithers, M.J. J.Chem Soc. (C) 1968, 715-725.
16. Matsuura F., Hamada Y., Shioiri T. Tetrahedron. 50:1994;9457-9470.
17. Henrot S., Larcheveque M., Petit Y. Synth. Commun. 16:1986;183-190.
18. Fushiya, S.; Hamada, Y.; Nakatsuyama, S; Kanuma, N.; Nozoe, S. Chem.Lett. 1981, 909-912.
19. While preparing the nicotianamine model compound 22 initially we protected the -COOH groups with benzyl ester and failed to get desired product during the course of desulfurization step with Raney nickel. Subsequently tert - butyl ester group was chosen.