Title:
EFFECTIVE PRODUCTION PROCESS FOR MUGINEIC ACID COMPOUND
Document Type and Number:
WIPO Patent Application WO/2008/059782
Kind Code:
A1
Abstract:
Disclosed is a process for producing a mugineic acid compound, which is shown
by the following scheme. STEP 1 STEP 2 STEP 3 STEP 4 wherein R1 and R2
independently represent a hydrogen atom or a hydroxyl group; R3 represents
a hydroxyl group or an amino group; R4 and R7 independently
represent a hydrogen atom or a protective group for a carboxyl group; R5
represents a protective group for an amino group; R6 represents a protective
group for a carboxyl group; and R8 represents -OR9 (wherein
R9 represents a protective group for a hydroxyl group) or -NHR10
(wherein R10 represents a protective group for an amino group)].
Inventors:
NAMBA KOSUKE (JP)
MURATA YOSHIKO (JP)
MURATA YOSHIKO (JP)
Application Number:
PCT/JP2007/071893
Publication Date:
May 22, 2008
Filing Date:
November 12, 2007
Export Citation:
Assignee:
SUNTORY LTD (JP)
NAMBA KOSUKE (JP)
MURATA YOSHIKO (JP)
NAMBA KOSUKE (JP)
MURATA YOSHIKO (JP)
International Classes:
C07D205/04
Other References:
OHFUNE Y. ET AL.: "ONE-STEP N-ALKYLATION OF alpha-AMINO ACIDS BY MEANS OF SODIUM CYANOBOROHYDRIDE", PEPTIDE CHEMISTRY, 1983, pages 89 - 92, XP008133458
OHFUNE Y. ET AL.: "AN EFFICIENT ONE-STEP REDUCTIVE N-MONOALKYLATION OF alpha-AMINO ACIDS", CHEMISTRY LETTERS, vol. 13, no. 3, 1984, pages 441 - 444, XP008110655
FUSHIYA S. ET AL.: "SYNTHESIS OF NICOTIANAMINE AND A RELATED COMPOUND, DERIVATIVES OF AZETIDINE-2-CARBOXYLIC ACID", HETEROCYCLES, vol. 15, no. 2, 1981, pages 819 - 822, XP008111258
RIPPERGER H.: "The Normalizing Factor for the Tomato Mutant chloronerva. XXIII[1] Deaminonicotianamine and 2-Decarboxynicotianamine", JOURNAL OF PRAKT. CHEMIE, vol. 328, no. 5-6, 1986, pages 719 - 723, XP008111268
MARSCHNER, H. ET AL., JOURNAL OF PLANT NUTRITION, vol. 9TH, 1986, pages 695 - 713
TAKEMOTO, T. ET AL., PROCEEDINGS OF THE JAPAN ACADEMY, vol. 54-B, 1978, pages 469 - 473
MA, J.F.; NOMOTO, K., PHYSIOLOGIA PLANTARUM, vol. 97TH, 1996, pages 609 - 617
NOMOTO, K. ET AL., CHIMIA, vol. 7TH, 1981, pages 249 - 250
OHFUNE, Y. ET AL., JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 103, 1981, pages 2409 - 2410
FUSHIYA, S. ET AL., CHEMISTRY LETTERS, 1981, pages 909 - 912
HAMADA, Y.; SHIOIRI, T., THE JOURNAL OF ORGANIC CHEMISTRY, vol. 51ST, 1986, pages 5489 - 5490
MATSUURA, F. ET AL., TETRAHEDRON, vol. 49TH, 1993, pages 8211 - 8222
MIYAKOSHI, K. ET AL., TETRAHEDRON, vol. 57TH, 2001, pages 3355 - 3360
SINGH, S. ET AL., TETRAHEDRON LETTERS, vol. 46TH, 2005, pages 1419 - 1421
NISHIMARU, T. ET AL., PEPTIDE SCIENCE, vol. 42, 2006, pages 263 - 266
NOMOTO, K., CHEMIA, vol. 7, 1981, pages 249
TAKAGI, S. ET AL., JOURNAL OF PLANT NUTRITION, 1984, pages 469 - 477
MURATA, Y. ET AL., PLANT JOURNAL, vol. 46TH, 2006, pages 563 - 572
PLANT J., vol. 46, 2006, pages 563 - 572
OHFUNE Y. ET AL.: "AN EFFICIENT ONE-STEP REDUCTIVE N-MONOALKYLATION OF alpha-AMINO ACIDS", CHEMISTRY LETTERS, vol. 13, no. 3, 1984, pages 441 - 444, XP008110655
FUSHIYA S. ET AL.: "SYNTHESIS OF NICOTIANAMINE AND A RELATED COMPOUND, DERIVATIVES OF AZETIDINE-2-CARBOXYLIC ACID", HETEROCYCLES, vol. 15, no. 2, 1981, pages 819 - 822, XP008111258
RIPPERGER H.: "The Normalizing Factor for the Tomato Mutant chloronerva. XXIII[1] Deaminonicotianamine and 2-Decarboxynicotianamine", JOURNAL OF PRAKT. CHEMIE, vol. 328, no. 5-6, 1986, pages 719 - 723, XP008111268
MARSCHNER, H. ET AL., JOURNAL OF PLANT NUTRITION, vol. 9TH, 1986, pages 695 - 713
TAKEMOTO, T. ET AL., PROCEEDINGS OF THE JAPAN ACADEMY, vol. 54-B, 1978, pages 469 - 473
MA, J.F.; NOMOTO, K., PHYSIOLOGIA PLANTARUM, vol. 97TH, 1996, pages 609 - 617
NOMOTO, K. ET AL., CHIMIA, vol. 7TH, 1981, pages 249 - 250
OHFUNE, Y. ET AL., JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 103, 1981, pages 2409 - 2410
FUSHIYA, S. ET AL., CHEMISTRY LETTERS, 1981, pages 909 - 912
HAMADA, Y.; SHIOIRI, T., THE JOURNAL OF ORGANIC CHEMISTRY, vol. 51ST, 1986, pages 5489 - 5490
MATSUURA, F. ET AL., TETRAHEDRON, vol. 49TH, 1993, pages 8211 - 8222
MIYAKOSHI, K. ET AL., TETRAHEDRON, vol. 57TH, 2001, pages 3355 - 3360
SINGH, S. ET AL., TETRAHEDRON LETTERS, vol. 46TH, 2005, pages 1419 - 1421
NISHIMARU, T. ET AL., PEPTIDE SCIENCE, vol. 42, 2006, pages 263 - 266
NOMOTO, K., CHEMIA, vol. 7, 1981, pages 249
TAKAGI, S. ET AL., JOURNAL OF PLANT NUTRITION, 1984, pages 469 - 477
MURATA, Y. ET AL., PLANT JOURNAL, vol. 46TH, 2006, pages 563 - 572
PLANT J., vol. 46, 2006, pages 563 - 572
Attorney, Agent or Firm:
IWATANI, Ryo (1-31 Dojima 2-chome, Kita-ku, Osaka-sh, Osaka 03, JP)
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