Total synthesis and cytotoxicity studies of a cyclic depsipeptide with proposed structure of palau'amide

被引:42
作者
Zou, B [1 ]
Long, K [1 ]
Ma, DW [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/ol051685g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of a cyclic depsipeptide with proposed structure of palau'amide is achieved, which features a stereoselective elaboration of its 5,7-dihydroxy-2,6-dimethyidodec-2-en-11-ynoic acid unit. The synthetic compound has potent cytotoxicity against three tumor cell lines but different rotation and NMR data compared to those reported for palau'amide, which implies that its conformation is close to that of palau'amide but that some stereochemistry in palau'amide was misassigned.
引用
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页码:4237 / 4240
页数:4
相关论文
共 31 条
[1]   Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A [J].
Chen, JH ;
Forsyth, CJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (33) :12067-12072
[2]   Total synthesis of apratoxin A [J].
Chen, JH ;
Forsyth, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (29) :8734-8735
[3]  
CIOMMER M, 1991, SYNLETT, P593
[4]   1,3-ASYMMETRIC INDUCTION IN THE ALDOL ADDITION-REACTIONS OF METHYL KETONE ENOLATES AND ENOLSILANES TO BETA-SUBSTITUTED ALDEHYDES - A MODEL FOR CHIRALITY TRANSFER [J].
EVANS, DA ;
DUFFY, JL ;
DART, MJ .
TETRAHEDRON LETTERS, 1994, 35 (46) :8537-8540
[5]   Studies directed toward the total synthesis of scytophycin C: Synthesis of the C(1)-C(18) fragment of scytophycin C [J].
Grieco, PA ;
Speake, JD .
TETRAHEDRON LETTERS, 1998, 39 (11) :1275-1278
[6]   CHIRAL SYNTHESIS OF POLYKETIDE-DERIVED NATURAL-PRODUCTS .32. SYNTHESIS OF ERYTHRONOLIDE A VIA A VERY EFFICIENT MACROLACTONIZATION UNDER USUAL ACYLATION CONDITIONS WITH THE YAMAGUCHI REAGENT [J].
HIKOTA, M ;
SAKURAI, Y ;
HORITA, K ;
YONEMITSU, O .
TETRAHEDRON LETTERS, 1990, 31 (44) :6367-6370
[7]   RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].
INANAGA, J ;
HIRATA, K ;
SAEKI, H ;
KATSUKI, T ;
YAMAGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993
[8]  
KROHN K, 1985, LIEBIGS ANN CHEM, P1311
[9]  
LEUSCH H, 2002, BIOORGAN MED CHEM, V10, P1973
[10]   Isolation and structure of the cytotoxin lyngbyabellin B and absolute configuration of lyngbyapeptin A from the marine cyanobacterium Lyngbya majuscula [J].
Luesch, H ;
Yoshida, WY ;
Moore, RE ;
Paul, VJ .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (10) :1437-1439