Synthesis of enantiomerically pure (3R,4R,5R)-4-hydroxy isoleucine lactone

被引：12

作者：

Kassem, T

Wehbe, J

Rolland-Fulcrand, V

Rolland, M

Roumestant, ML

Martinez, J

机构：

[1] Univ Montpellier 1, Lab Aminoacides Peptides & Prot, F-34095 Montpellier 5, France

[2] Univ Montpellier 2, Lab Aminoacides Peptides & Prot, F-34095 Montpellier, France

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 19期

关键词：

D O I：

10.1016/S0957-4166(01)00465-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A short four-step synthesis of (3R,4R,5R)-4-hydroxyisoleucine lactone with total control of stereochemistry is reported, the key intermediate being the didehydroamino acid derivative arising from an aldol dehydration reaction between a glycine anion equi, lent and butan-2,3-dione. (C) 2001 Published by Elsevier Science.

引用

收藏

页码：2657 / 2661

页数：5

相关论文

共 18 条

[1] STEREOCHEMISTRY OF THE 4-HYDROXYISOLEUCINE FROM TRIGONELLA-FOENUM-GRAECUM [J].

ALCOCK, NW ;

CROUT, DHG ;

GREGORIO, MVM ;

LEE, E ;

PIKE, G ;

SAMUEL, CJ .

PHYTOCHEMISTRY, 1989, 28 (07) :1835-1841

[2] Some of the amino acid chemistry going on in the Laboratory of Amino acids, Peptides and Proteins [J].

Bouifraden, S ;

Drouot, C ;

El Hadrami, M ;

Guenoun, F ;

Lecointe, L ;

Mai, N ;

Paris, M ;

Pothion, C ;

Sadoune, M ;

Sauvagnat, B ;

Amblard, M ;

Aubagnac, JL ;

Calmes, M ;

Chevallet, P ;

Daunis, J ;

Enjalbal, C ;

Fehrentz, JA ;

Lamaty, F ;

Lavergne, JP ;

Lazaro, R ;

Rolland, V ;

Roumestant, ML ;

Viallefont, P ;

Vidal, Y ;

Martinez, J .

AMINO ACIDS, 1999, 16 (3-4) :345-379

[3] EFFICIENT ASYMMETRIC-SYNTHESIS OF AMINO-ACIDS THROUGH HYDROGENATION OF THE DIDEHYDROAMINO ACID RESIDUE IN CYCLIC IMINO-ESTER DERIVATIVES [J].

CATIVIELA, C ;

DIAZDEVILLEGAS, MD ;

GALVEZ, JA .

TETRAHEDRON-ASYMMETRY, 1992, 3 (04) :567-572

[4]

DARDENNE G, 1986, B RECH AGRON GEMBLOU, V21, P125

[5] Enamino ester reduction:: A short enantioselective route to pyrrolizidine and indolizidine alkaloids.: Synthesis of (+)-laburnine, (+)-tashiromine, and (-)-isoretronecanol [J].

David, O ;

Blot, J ;

Bellec, C ;

Fargeau-Bellassoued, MC ;

Haviari, G ;

Célérier, JP ;

Lhommet, G ;

Gramain, JC ;

Gardette, D .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3122-3131

[6] 2-HYDROXY-3-PINANONE AS CHIRAL AUXILIARY IN THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

ELACHQAR, A ;

BOUMZEBRA, M ;

ROUMESTANT, ML ;

VIALLEFONT, P .

TETRAHEDRON, 1988, 44 (17) :5319-5332

[7] Efficient synthesis of dehydroamino acid derivatives [J].

Ferreira, PMT ;

Maia, HLS ;

Monteiro, LS .

TETRAHEDRON LETTERS, 1998, 39 (51) :9575-9578

[8] 4-HYDROXYISOLEUCINE FROM SEED OF TRIGONELLA-FOENUM-GRAECUM [J].

FOWDEN, L ;

PRATT, HM ;

SMITH, A .

PHYTOCHEMISTRY, 1973, 12 (07) :1707-1711

[9]

GIEREN A, 1974, LIEBIGS ANN CHEM, P1561, DOI 10.1002/jlac.197419741004

[10]

GULL R, 1985, SYNTHESIS-STUTTGART, P1052