TOTAL SYNTHESIS OF 2'-DEOXYMUGINEIC ACID AND NICOTIANAMINE

被引：42

作者：

MATSUURA, F ^{[1
]}

HAMADA, Y ^{[1
]}

SHIOIRI, T ^{[1
]}

机构：

[1] NAGOYA CITY UNIV,FAC PHARMACEUT SCI,MIZUHO KU,NAGOYA,AICHI 467,JAPAN

来源：

TETRAHEDRON | 1994年 / 50卷 / 31期

关键词：

D O I：

10.1016/S0040-4020(01)85520-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

引用

页码：9457 / 9470

页数：14

共 27 条

[1]

CARISEN PH, 1981, J ORG CHEM, V46, P3936

[2] SYNTHESIS OF AVENIC ACID A AND 2'-DEOXYMUGINEIC ACID, AMINO-ACIDS POSSESSING AN IRON CHELATING ACTIVITY [J].

FUSHIYA, S ;

SATO, Y ;

NAKATSUYAMA, S ;

KANUMA, N ;

NOZOE, S .

CHEMISTRY LETTERS, 1981, (07) :909-912

[3]

FUSHIYA S, 1981, HETEROCYCLES, V15, P819

[4] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .67. A GENERAL-SYNTHESIS OF DERIVATIVES OF OPTICALLY PURE 2-(1-AMINOALKYL)THIAZOLE-4-CARBOXYLIC ACIDS [J].

HAMADA, Y ;

SHIBATA, M ;

SUGIURA, T ;

KATO, S ;

SHIOIRI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1252-1255

[5] A NEW STEREOSELECTIVE SYNTHESIS OF A GAMMA-AZETIDINYL-BETA-HYDROXY-ALPHA-AMINO ACID MOIETY OF MUGINEIC ACID - A FORMAL SYNTHESIS OF MUGINEIC ACID [J].

HAMADA, Y ;

IWAI, K ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1990, 31 (35) :5041-5042

[6] SYNTHESIS OF MUGINEIC ACID THROUGH DIRECT C-ACYLATION USING DIPHENYL PHOSPHORAZIDATE [J].

HAMADA, Y ;

SHIORI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) :5489-5490

[7] SYNTHESIS OF (4R)-D,L-[4-H-2]HOMOSERINE AND (4S)-D,L-[4-H-2]HOMOSERINE LACTONES [J].

KALVIN, DM ;

WOODARD, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2259-2263

[8] EFFICIENT SYNTHESIS OF PHYTOSIDEROPHORES, 3-EPI-HYDROXYMUGINEIC ACID AND DISTICHONIC ACID-A [J].

MATSUURA, F ;

HAMADA, Y ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1992, 33 (51) :7921-7924

[9] A SYNTHESIS OF A GAMMA-AZETIDINYL-BETA-HYDROXY-ALPHA-AMINO ACID-DERIVATIVE, A KEY INTERMEDIATE FOR THE SYNTHESIS OF MUGINEIC ACID [J].

MATSUURA, F ;

HAMADA, Y ;

SHIOIRI, T .

TETRAHEDRON-ASYMMETRY, 1992, 3 (08) :1069-1074

[10] TOTAL SYNTHESIS OF MUGINEIC ACID - EFFICIENT USE OF THE PHENYL GROUP AS THE CARBOXYL SYNTHON [J].

MATSUURA, F ;

HAMADA, Y ;

SHIORI, T .

TETRAHEDRON, 1993, 49 (36) :8211-8222

← 1 2 3 →