Fumiyoshi Matsuura

Total synthesis of mugineic acid. Efficient use of the phenyl group as the carboxyl synthon

Abstract Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from readily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6). The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.

Synthesis and application of new chiral bidentate phosphine, 2,7-di-tert-butyl-9,9-dimethyl-4,5-bis(methylphenylphosphino)xanthene

Abstract New optically active bidentate phosphines, (S,S)- and (R,R)-2,7-di-tert-butyl-9,9-dimethyl-4,5-bis(methylphenylphosphino)xanthenes ( (S,S)- 1 and (R,R)- 1 ), were prepared through resolution of the corresponding phosphine oxides using (R,R)-(−)-dibenzoyl-tartaric acid and a preliminary experiment on asymmetric synthesis using an allyl substrate proved the utility of the new bidentate phosphines.

Total synthesis of 2′-deoxymugineic acid and nicotianamine

Abstract Stereoselective total synthesis of the unique phytosiderophores, 2′-deoxymugineic acid(4) and nicotianamine (5), has been achieved from the β-tyrosine derivative 21 using its aryl groups as the carboxyl synthon.

Total Syntheses of Phytosiderophores, 3-Epi-Hydroxymugineic Acid, Distichonic Acid A, and 2′-Hydroxynicotianamine

Abstract First total syntheses of the unique phytosiderophores, 3-epi-hydroxymugineic acid ( 2 ), distichonic acid A ( 3 ), and 2′-hydroxynicotianamine ( 5 ), have been efficiently achieved from the same intermediates used for the synthesis of mugineic acid ( 1 ), the typical phytosiderophore.

An efficient synthesis of polyoxamic acid utilizing the aryl group as the carboxyl synthon. A new approach to polyhydroxyamino acids

Abstract Polyoxamic acid ( 1 ), an amino acid moiety of antifungal antibiotics polyoxins, has been efficiently synthesized from Boc-(R)-4-hydroxyphenylglycine ( 3 ) utilizing its aryl group as the carboxyl synthon.

Total synthesis of microginin, an angiotensin-converting enzyme inhibitory pentapeptide from the blue-green alga Microcystis aeruginosa

Abstract Microginin, an angiotensin-converting enzyme inhibitory peptide isolated form the blue-green alga Microcystis aeruginosa , and its three diastereoisomers were efficiently synthesized, which unequivocally established the absolute stereostructure of microginin to be 1d .

Efficient synthesis of mugineic acid, a typical phytosiderophore, utilizing the phenyl group as the carboxyl synthon☆

Abstract Stereoselective total synthesis of mugineic acid, a unique phytosiderophore from roots of barley, has been achieved from (2R,3R)- and (2S,3S)-2,3-epoxycinnamyl alcohols employing the phenyl group as the carboxyl synthon.

Efficient synthesis of phytosiderophores, 3-epi-hydroxymugineic acid and distichonic acid A

Abstract Synthesis of 3-epi-hydroxymugineic acid (2) and distichonic acid A (3), phytosiderophores from graminaceous plants, has been efficiently achieved for the first time.

A synthesis of a γ-azetidinyl-β-hydroxy-α-amino acid derivative, a key intermediate for the synthesis of mugineic acid

Abstract The γ-azetidinyl-β-hydroxy-α-amino acid derivative 2, a key intermediate for the total synthesis of mugineic acid (1), was stereoselectively prepared from readily available (2R,3R)-epoxysuccinic acid (3).