SYNTHETIC STUDIES TOWARDS CYCLIC-PEPTIDES - CONCISE SYNTHESIS OF THIAZOLINE AND THIAZOLE CONTAINING AMINO-ACIDS

被引：92

作者：

NORTH, M ^{[1
]}

PATTENDEN, G ^{[1
]}

机构：

[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 24期

关键词：

D O I：

10.1016/S0040-4020(01)81482-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Concise and efficient syntheses of optically pure thiazoline and thiazole containing amino acids of the constitution (26) and (27), based on simple condensation reactions between cysteine esters and N-protected imino ethers (22) and (25) derived from chiral amino acids, are described. The synthetic procedures are compatible with a range of amino acid side chains and protecting groups, and allow the preparation of a variety of small optically pure peptides i.e. (32) and (34) suitable for elaboration to naturally occurring cyclic peptides e.g. the lissoclinamides (3) and (4). © 1990.

引用

收藏

页码：8267 / 8290

页数：24

相关论文

共 42 条

[1] A NEW SYNTHETIC ROUTE TO (+/-)-FORSKOLIN [J].

BEGLEY, MJ ;

CHESHIRE, DR ;

HARRISON, T ;

HUTCHINSON, JH ;

MYERS, PL ;

PATTENDEN, G .

TETRAHEDRON, 1989, 45 (16) :5215-5246

[2] AN EFFICIENT TOTAL SYNTHESIS OF AGROBACTIN AND ITS GALLIUM(III) CHELATE [J].

BERGERON, RJ ;

MCMANIS, JS ;

DIONIS, JB ;

GARLICH, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15) :2780-2782

[3]

CARSON JF, 1981, SYNTHESIS-STUTTGART, P268

[4] NEW CYCLIC-PEPTIDES WITH CYTO-TOXIC ACTIVITY FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].

DEGNAN, BM ;

HAWKINS, CJ ;

LAVIN, MF ;

MCCAFFREY, EJ ;

PARRY, DL ;

VANDENBRENK, AL ;

WATTERS, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (06) :1349-1354

[5] MARINE NATURAL-PRODUCTS [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1988, 5 (06) :613-663

[6] PROPOSED STRUCTURE OF THE CYCLIC PEPTIDE DOLASTATIN-3, A POWERFUL CELL-GROWTH INHIBITOR, SHOULD BE REVISED [J].

HAMADA, Y ;

KOHDA, K ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1984, 25 (46) :5303-5306

[7] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .51. A SYNTHESIS OF ASCIDIACYCLAMIDE, A CYTO-TOXIC CYCLIC PEPTIDE FROM ASCIDIAN - DETERMINATION OF ITS ABSOLUTE-CONFIGURATION [J].

HAMADA, Y ;

KATO, S ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1985, 26 (27) :3223-3226

[8] 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

[9] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .56. TOTAL SYNTHESES OF PATELLAMIDES-B AND PATELLAMIDES-C, CYTO-TOXIC CYCLIC-PEPTIDES FROM A TUNICATE .2. THEIR REAL STRUCTURES HAVE BEEN DETERMINED BY THEIR SYNTHESES [J].

HAMADA, Y ;

SHIBATA, M ;

SHIOIRI, T .

TETRAHEDRON LETTERS, 1985, 26 (42) :5159-5162

[10] 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

← 1 2 3 4 5 →