FORMATION OF OXAZOLINES AND THIAZOLINES IN PEPTIDES BY THE MITSUNOBU REACTION

被引:108
作者
GALEOTTI, N
MONTAGNE, C
PONCET, J
JOUIN, P
机构
关键词
BETA-HYDROXY ALPHA-AMINO ACIDS; PEPTIDE-MIMICS;
D O I
10.1016/S0040-4039(00)78864-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Mitsunobu reaction was efficiently used to introduce oxazolines and thiazolines in the peptide backbone. The reaction proceeded from beta-hydroxy alpha-amino acid-containing peptides at room temperature in 58-72% isolated yields.
引用
收藏
页码:2807 / 2810
页数:4
相关论文
共 17 条
[1]  
CASTRO B, 1975, TETRAHEDRON LETT, P1219
[2]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .58, A SYNTHESIS OF PATELLAMIDE-A, A CYTOTOXIC CYCLIC PEPTIDE FROM A TUNICATE - REVISION OF ITS PROPOSED STRUCTURE [J].
HAMADA, Y ;
SHIBATA, M ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1985, 26 (52) :6501-6504
[3]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .55. TOTAL SYNTHESES OF PATELLAMIDES-B AND PATELLAMIDES-C, CYTO-TOXIC CYCLIC-PEPTIDES FROM A TUNICATE .1. THEIR PROPOSED STRUCTURES SHOULD BE CORRECTED [J].
HAMADA, Y ;
SHIBATA, M ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1985, 26 (42) :5155-5158
[4]   SYNTHETIC STUDIES OF BACTIRACIN .4. SYNTHESIS OF THIAZOLINE PEPTIDES BY IMINOETHER COUPLING METHOD [J].
HIROTSU, Y ;
SHIBA, T ;
KANEKO, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (12) :2945-+
[5]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .64. TOTAL SYNTHESIS OF ULITHIACYCLAMIDE, A STRONG CYTOTOXIC CYCLIC PEPTIDE FROM MARINE TUNICATES [J].
KATO, S ;
HAMADA, Y ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1986, 27 (23) :2653-2656
[6]  
Kemp D. S., 1979, PEPTIDES ANAL SYNTHE, V1, P315
[7]   FACILE REGIOSELECTIVE FORMATION OF THIOPEPTIDE LINKAGES FROM OLIGOPEPTIDES WITH NEW THIONATION REAGENTS [J].
LAJOIE, G ;
LEPINE, F ;
MAZIAK, L ;
BELLEAU, B .
TETRAHEDRON LETTERS, 1983, 24 (36) :3815-3818
[8]  
LOCKHART MI, 1954, NATURE, V173, P536
[9]   PREPARATION OF ESTERS OF CARBOXYLIC AND PHOSPHORIC ACID VIA QUATERNARY PHOSPHONIUM SALTS [J].
MITSUNOBU, O ;
YAMADA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (10) :2380-+
[10]   STUDIES ON HYDROXY AMINO-ACIDS .6. FORMATION OF OXAZOLINE DERIVATIVES FROM N-ACYL-BETA-HYDROXY AMINO-ACID PEPTIDES [J].
NAKAJIMA, K ;
KAWAI, H ;
TAKAI, M ;
OKAWA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (04) :917-920