Total synthesis of the thiazoline-based cyclopeptide cyclodidemnamide

被引:27
作者
Boden, CDJ [1 ]
Norley, MC [1 ]
Pattenden, G [1 ]
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
关键词
D O I
10.1016/S0040-4039(96)02099-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A total synthesis of the proposed structure 1 for cyclodidemnamide from the marine ascidian Didemnum molle is described, which features the novel double, sequential Formation of chiral thiazoline and oxazoline rings as the key stratagem. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:9111 / 9114
页数:4
相关论文
共 12 条
[1]   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
[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]   STUDIES OF AUSTRALIAN ASCIDIANS .4. MOLLAMIDE, A CYTOTOXIC CYCLIC HEPTAPEPTIDE FROM THE COMPOUND ASCIDIAN DIDEMNUM MOLLE [J].
CARROLL, AR ;
BOWDEN, BF ;
COLL, JC ;
HOCKLESS, DCR ;
SKELTON, BW ;
WHITE, AH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (01) :61-69
[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]   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
[6]   SYNTHETIC STUDIES ON BACITRACIN .7. ISOMERIZATION OF AMINO ACID COMPONENTS OF THIAZOLINE PEPTIDES [J].
HIROTSU, Y ;
SHIBA, T ;
KANEKO, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1970, 43 (06) :1870-+
[7]   OXIDATION AND ACID ISOMERIZATION OF BACITRACINA [J].
KONIGSBERG, W ;
HILL, RJ ;
CRAIG, LC .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (10) :3867-&
[8]   CYCLIC-PEPTIDES FROM THE ASCIDIAN LISSOCLINUM-PATELLA - CONFORMATIONAL-ANALYSIS OF PATELLAMIDE-D BY X-RAY-ANALYSIS AND MOLECULAR MODELING [J].
SCHMITZ, FJ ;
KSEBATI, MB ;
CHANG, JS ;
WANG, JL ;
HOSSAIN, MB ;
VANDERHELM, D ;
ENGEL, MH ;
SERBAN, A ;
SILFER, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3463-3472
[9]   CYCLODIDEMNAMIDE - A NEW CYCLIC HEPTAPEPTIDE FROM THE MARINE ASCIDIAN DIDEMNUM MOLLE [J].
TOSKE, SG ;
FENICAL, W .
TETRAHEDRON LETTERS, 1995, 36 (46) :8355-8358
[10]   SYNTHESIS OF PEPTIDE THIAZOLINES FROM BETA-HYDROXYTHIOAMIDES - AN INVESTIGATION OF RACEMIZATION IN CYCLODEHYDRATION PROTOCOLS [J].
WIPF, P ;
FRITCH, PC .
TETRAHEDRON LETTERS, 1994, 35 (30) :5397-5400