ISOLATION, STRUCTURE, AND SYNTHESIS OF DOLASTATIN-D, A CYTOTOXIC CYCLIC DEPSIPEPTIDE FROM THE SEA HARE DOLABELLA-AURICULARIA

被引:58
作者
SONE, H [1 ]
NEMOTO, T [1 ]
ISHIWATA, H [1 ]
OJIKA, M [1 ]
YAMADA, K [1 ]
机构
[1] NAGOYA UNIV,FAC SCI,DEPT CHEM,NAGOYA 464,JAPAN
关键词
D O I
10.1016/S0040-4039(00)61356-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dolastatin D (1), a cytotoxic cyclic depsipeptide possessing the novel beta-amino acid (2R,3R)-3-amino-2-methylbutanoic acid [(2R,3R)-3] as a component, has been isolated from the Japanese sea hare Dolabella auricularia. The absolute stereostructure of 1 was elucidated on the basis of spectroscopic analysis and chemical degradation and was further confirmed by synthesis.
引用
收藏
页码:8449 / 8452
页数:4
相关论文
共 21 条
[1]   ASYMMETRIC SYNTHESES OF 3-AMINO-2-METHYLPENTANOIC ACIDS - CONFIGURATIONS OF THE BETA-AMINO ACID IN MAJUSCULAMIDE C, 57-NORMAJUSCULAMIDE-C AND DOLASTATINS 11 AND 12 [J].
BATES, RB ;
GANGWAR, S .
TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :69-72
[2]   PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].
BODEN, EP ;
KECK, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395
[3]   STRUCTURE OF MAJUSCULAMIDE-C, A CYCLIC DEPSIPEPTIDE FROM LYNGBYA-MAJUSCULA [J].
CARTER, DC ;
MOORE, RE ;
MYNDERSE, JS ;
NIEMCZURA, WP ;
TODD, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) :236-241
[4]  
CASTRO B, 1975, TETRAHEDRON LETT, P1219
[5]   AMINO-ACIDS OF THE MURCHISON METEORITE .2. 5 CARBON ACYCLIC PRIMARY BETA-AMINO,GAMMA-AMINO AND DELTA-AMINO ALKANOIC ACIDS [J].
CRONIN, JR ;
PIZZARELLO, S ;
YUEN, GU .
GEOCHIMICA ET COSMOCHIMICA ACTA, 1985, 49 (11) :2259-2265
[6]   DIASTEREOSELECTIVE ALKYLATION OF 3-AMINOBUTANOIC ACID IN THE 2-POSITION [J].
ESTERMANN, H ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1988, 71 (07) :1824-1839
[7]   EFFICIENT TOTAL SYNTHESIS OF DIDEMNINS A AND B [J].
HAMADA, Y ;
KONDO, Y ;
SHIBATA, M ;
SHIOIRI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :669-673
[8]   AMINO-ACIDS AND PEPTIDES .21. SYNTHESIS OF A CONGENER OF THE CYCLOHEXADEPSIPEPTIDE ANTIBIOTIC, MONAMYCIN [J].
HASSALL, CH ;
JOHNSON, WH ;
THEOBALD, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1451-1454
[9]   ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS .2. PREPARATION OF THE LIKE STEREOISOMERS OF 2-METHYL-3-AMINOBUTANOIC ACID AND 2-BENZYL-3-AMINOBUTANOIC ACID [J].
JUARISTI, E ;
ESCALANTE, J ;
LAMATSCH, B ;
SEEBACH, D .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2396-2398
[10]  
Kobayashi J., 1992, ALKALOIDS, V41, P41