Total Synthesis of 2'-Deoxymugineic Acid, the Metal Chelator Excreted from Wheat Root

Journal of the American Chemical Society

Volumn 103, Issue 9, 1981, Pages 2409-2410

  Ohfune, Yasufumi ^a   Tomita, Masako ^a   Nomoto, Kyosuke ^a  

^a SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000860251     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00399a046     Document Type: Article

References (10)

1. Brown, J. C. Anna. Rev. Plant Physiol. 1956, 7, 171.
2. Takagi, S. Soil. Sci. Plant Nutr. (Tokyo) 1976, 22, 423.
3. Takemoto, T.; Nomoto, K.; Fushiya, S.; Ouchi, R.; Kusano, G.; Hikino, H.; Takagi, S.; Matsuura, Y.; Kakudo, M. Proc. Jpn. Acad., Ser. B 1978, 54, 469.
4. Nomoto, K.; Yoshioka, Y.; Arima, M.; Takemoto, T.; Fushiya, Y.; Takagi, S. Helv. Chim. Acta, in press.
5. Fushiya, S.; Sato, S.; Nozoe, S.; Nomoto, K.; Takemoto, T. Tetrahedron Lett. 1980, 3071.
6. Takagi, S., to be published.
7. Metal chelation of mugineic acid was confirmed by X-ray crystallographic analysis using Cu2+ (1:1 complex): Nomoto, K.; Mino, Y.; Ishida, T.; Yoshioka, H.; Ota, N.; Inoue, M.; Takagi, S.; Takemoto, T. J. Chem. Soc., Chem. Commun., in press.
8. Sangster, A. W.; Thomas, S. E.; Tingling, N. L. Tetrahedron 1975, 31, 1135. Schellenbergh, K. A. J. Org. Chem. 1963, 28, 3259. Biemann, K. “Mass Spectrometry Organic Chemical Applications”; McGraw-Hill: New York, 1962; p 358.
9. Collum, D. B.; McDonald, J. H., III; Still, W. C. J. Am. Chem. Soc. 1980, 102, 2118.
10. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897. Recently Nozoe et al. have used a similar sequence of reactions for the preparation of a related compound: Fushiya, S.; Sato, Y.; Nozoe, S. Chem. Lett. 1980, 1215.