Total synthesis of cyclomarin C

被引:70
作者
Wen, SJ [1 ]
Yao, ZJ [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/ol049065n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.
引用
收藏
页码:2721 / 2724
页数:4
相关论文
共 27 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]   A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan [J].
Aurelio, L ;
Brownlee, RTC ;
Hughes, AB .
ORGANIC LETTERS, 2002, 4 (21) :3767-3769
[3]  
Bakke M, 1999, SYNTHESIS-STUTTGART, P1671
[4]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[5]   PYBOP - A NEW PEPTIDE COUPLING REAGENT DEVOID OF TOXIC BY-PRODUCT [J].
COSTE, J ;
LENGUYEN, D ;
CASTRO, B .
TETRAHEDRON LETTERS, 1990, 31 (02) :205-208
[6]  
DIAGOMESEGUER J, 1980, SYNTHESIS-STUTTGART, P547
[7]   STEREOCONTROLLED SYNTHESIS OF BETA-HYDROXYPHENYLALANINE AND BETA-HYDROXYTYROSINE DERIVATIVES [J].
EASTON, CJ ;
HUTTON, CA ;
ROSELT, PD ;
TIEKINK, ERT .
TETRAHEDRON, 1994, 50 (24) :7327-7340
[8]   Synthesis and absolute stereochemical assignment of (+)-miyakolide [J].
Evans, DA ;
Ripin, DHB ;
Halstead, DP ;
Campos, KR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) :6816-6826
[9]   CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA .
TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144
[10]   THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA ;
DOROW, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030