Concise synthesis of stereodefined, thiazole -: containing cyclic hexa- and octapeptide relatives of the Lissoclinums, via cyclooligomerisation reactions

被引:36
作者
Bertram, A [1 ]
Blake, AJ [1 ]
de Turiso, FGL [1 ]
Hannam, JS [1 ]
Jolliffe, KA [1 ]
Pattenden, G [1 ]
Skae, M [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
关键词
Lissoclinum; cyclooligomerisation; thiazole;
D O I
10.1016/S0040-4020(03)00821-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a range of thiazole containing cyclic peptides using cyclooligomerisation reactions of amino acid substituted thiazole monomers and by macrolactamisation procedures is reported. The synthetic approaches lead to high yields of novel 18- and 24-membered ring analogues of the naturally occurring Lissoclinum families of cyclic peptides found in marine organisms and algae. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6979 / 6990
页数:12
相关论文
共 40 条
[1]   REINVESTIGATION OF A MODIFIED HANTZSCH THIAZOLE SYNTHESIS [J].
AGUILAR, E ;
MEYERS, AI .
TETRAHEDRON LETTERS, 1994, 35 (16) :2473-2476
[2]  
Bernhardt PV, 2002, CHEM-EUR J, V8, P1527, DOI 10.1002/1521-3765(20020402)8:7<1527::AID-CHEM1527>3.3.CO
[3]  
2-6
[4]  
Bertram A, 2000, SYNLETT, P1519
[5]  
Bertram A, 2002, HETEROCYCLES, V58, P521
[6]  
Bertram A, 1999, SYNLETT, P1723
[7]   Total synthesis and assignment of configuration of the thiazoline-based cyclopeptide cyclodidemnamide isolated from the sea squirt Didemnum molle [J].
Boden, CDJ ;
Norley, M ;
Pattenden, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (06) :883-888
[8]   CYCLOPEPTIDES FROM ASCIDIANS - TOTAL SYNTHESIS OF LISSOCLINAMIDE-4, AND A GENERAL STRATEGY FOR THE SYNTHESIS OF CHIRAL THIAZOLINE-CONTAINING MACROCYCLIC PEPTIDES [J].
BODEN, CDJ ;
PATTENDEN, G .
TETRAHEDRON LETTERS, 1995, 36 (34) :6153-6156
[9]   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
[10]   Total syntheses and re-assignment of configurations of the cyclopeptides lissoclinamide 4 and lissoclinamide 5 from Lissoclinum patella [J].
Boden, CDJ ;
Pattenden, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (06) :875-882