Total synthesis of the chlorinated marine natural product dysamide B

被引:48
作者
Durow, Amanda C. [1 ]
Long, G. Cliona [1 ]
O'Connell, Susan J. [1 ]
Willis, Christine L. [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
关键词
D O I
10.1021/ol062279f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Two approaches to the synthesis of (2S,4S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesis of the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an alpha, alpha-dichloro acid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.
引用
收藏
页码:5401 / 5404
页数:4
相关论文
共 32 条
[1]   A study of polychlorinated leucine derivatives:: synthesis of (2S,4S)-5,5-dichloroleucine [J].
Ardá, A ;
Jiménez, C ;
Rodríguez, J .
TETRAHEDRON LETTERS, 2004, 45 (16) :3241-3243
[2]   NEW AND IMPROVED METHODS FOR THE RADICAL DECARBOXYLATION OF ACIDS [J].
BARTON, DHR ;
CRICH, D ;
MOTHERWELL, WB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :939-941
[3]  
Borodine A., 1861, LIEBIGS ANN CHEM, V119, P121
[4]   The barbamide biosynthetic gene cluster: a novel marine cyanobacterial system of mixed polyketide synthase (PKS)-non-ribosomal peptide synthetase (NRPS) origin involving an unusual trichloroleucyl starter unit [J].
Chang, ZX ;
Flatt, P ;
Gerwick, WH ;
Nguyen, VA ;
Willis, CL ;
Sherman, DH .
GENE, 2002, 296 (1-2) :235-247
[5]   Solution-phase parallel synthesis of a pharmacophore library of HUN-7293 analogues: A general chemical mutagenesis approach to defining structure-function properties of naturally occurring cyclic (depsi)peptides [J].
Chen, Y ;
Bilban, M ;
Foster, CA ;
Boger, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5431-5440
[6]   N-METHYLAMINO ACIDS IN PEPTIDE-SYNTHESIS .7. STUDIES ON ENANTIOMERIC PURITY OF N-METHYLAMINO ACIDS PREPARED BY VARIOUS PROCEDURES [J].
CHEUNG, ST ;
BENOITON, NL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (05) :916-921
[7]   TOTAL SYNTHESIS OF (+)-DEMETHYLDYSIDENIN AND (-)-DEMETHYLISODYSIDENIN, HEXACHLORINATED AMINO-ACIDS FROM THE MARINE SPONGE DYSIDEA-HERBACEA - ASSIGNMENT OF ABSOLUTE STEREOCHEMISTRY [J].
DELASZLO, SE ;
WILLIARD, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (01) :199-203
[8]   Recent advances in the synthesis of diketopiperazines [J].
Dinsmore, CJ ;
Beshore, DC .
TETRAHEDRON, 2002, 58 (17) :3297-3312
[9]   New chlorinated metabolites from the tropical marine sponge Dysidea herbacea [J].
Dumdei, EJ ;
Simpson, JS ;
Garson, MJ ;
Byriel, KA ;
Kennard, CHL .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1997, 50 (02) :139-144
[10]   Characterization of the initial enzymatic steps of barbamide biosynthesis [J].
Flatt, Patricia M. ;
O'Connell, Susan J. ;
McPhail, Kerry L. ;
Zeller, Gloria ;
Willis, Christine L. ;
Sherman, David H. ;
Gerwick, William H. .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (06) :938-944