CYCLOPEPTIDES FROM ASCIDIANS - TOTAL SYNTHESIS OF LISSOCLINAMIDE-4, AND A GENERAL STRATEGY FOR THE SYNTHESIS OF CHIRAL THIAZOLINE-CONTAINING MACROCYCLIC PEPTIDES

被引:41
作者
BODEN, CDJ [1 ]
PATTENDEN, G [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
关键词
D O I
10.1016/0040-4039(95)01166-F
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the first synthesis of a chiral thiazoline-containing macrocyclic peptide, a total synthesis of lissoclinamide 4 2c, produced by the marine tunicate Lissoclinum patella, is described.
引用
收藏
页码:6153 / 6156
页数:4
相关论文
共 17 条
[1]   TOTAL SYNTHESIS OF LISSOCLINAMIDE-5, A CYTOTOXIC CYCLIC PEPTIDE FROM THE TUNICATE LISSOCLINUM-PATELLA [J].
BODEN, C ;
PATTENDEN, G .
TETRAHEDRON LETTERS, 1994, 35 (44) :8271-8274
[2]   THE SYNTHESIS OF OPTICALLY-ACTIVE THIAZOLINE AND THIAZOLE DERIVED PEPTIDES FROM N-PROTECTED ALPHA-AMINO-ACIDS [J].
BODEN, CDJ ;
PATTENDEN, G ;
YE, T .
SYNLETT, 1995, (05) :417-419
[3]  
CHEN S, 1991, TETRAHEDRON LETT, P6711
[4]   ASCIDIANS - PRODUCERS OF AMINO-ACID DERIVED METABOLITES [J].
DAVIDSON, BS .
CHEMICAL REVIEWS, 1993, 93 (05) :1771-1791
[5]   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
[6]   COMPARATIVE-STUDY OF SELECTED COUPLING REAGENTS IN DIPEPTIDE SYNTHESIS [J].
DUDASH, J ;
JIANG, JJ ;
MAYER, SC ;
JOULLIE, MM .
SYNTHETIC COMMUNICATIONS, 1993, 23 (03) :349-356
[7]   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
[8]   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
[9]   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
[10]   STRUCTURE-ACTIVITY-RELATIONSHIPS OF THE LISSOCLINAMIDES - CYTOTOXIC CYCLIC-PEPTIDES FROM THE ASCIDIAN LISSOCLINUM-PATELLA [J].
HAWKINS, CJ ;
LAVIN, MF ;
MARSHALL, KA ;
VANDENBRENK, AL ;
WATTERS, DJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1634-1638