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

被引：20

作者：

BATES, RB

GANGWAR, S

机构：

[1] Department of Chemistry, University of Arizona, Tucson

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 01期

关键词：

D O I：

10.1016/S0957-4166(00)86016-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first synthesis of 3-amino-2-methylpentanoic acids is reported. Comparison of the synthetic 2R,3R and 2L,3S acids with 3-amino-2-methylpentanoic acid obtained by degradation of the antifungal depsipeptide majusculamide C indicates that majusculamide C, 57-normajusculamide C, and the antitumor agents dolastatins 11 and 12 have the 2S,3R configurations at the chiral centers in their beta-amino acid component.

引用

页码：69 / 72

页数：4

共 8 条

[1] ENANTIOMERIC (Z)-CROTYLDIISOPINOCAMPHEYLBORANE AND (E)-CROTYLDIISOPINOCAMPHEYLBORANE - SYNTHESIS IN HIGH OPTICAL PURITY OF ALL 4 POSSIBLE STEREOISOMERS OF BETA-METHYLHOMOALLYL ALCOHOLS
BROWN, HC
BHAT, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (02) : 293 - 294
[2] STRUCTURE OF MAJUSCULAMIDE-C, A CYCLIC DEPSIPEPTIDE FROM LYNGBYA-MAJUSCULA
CARTER, DC
MOORE, RE
MYNDERSE, JS
NIEMCZURA, WP
TODD, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (02) : 236 - 241
[3] CARTER DC, 1980, THESIS U HAWAII
[4] DIRECT, HIGHLY EFFICIENT SYNTHESIS FROM (S)-(+)-PHENYLGLYCINE OF THE TAXOL AND TAXOTERE SIDE-CHAINS
DENIS, JN
CORREA, A
GREENE, AE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) : 6939 - 6942
[5] GANGWAR S, 1992, THESIS U ARIZONA
[6] ENANTIOMERIC 3,7-DIMETHYLOCTA-1,7-DIENES AS USEFUL CHIRAL BUILDING-BLOCKS - A NEW ACCESS TO BOTH OPTICAL-ANTIPODES OF NATURAL (E)-3,7-DIMETHYLOCT-2-ENE-1,8-DIOL AND (E)-3,7-DIMETHYLOCT-2-ENE-1,8-DICARBOXYLIC ACID
GIERSCH, W
SCHULTEELTE, KH
[J]. HELVETICA CHIMICA ACTA, 1990, 73 (03) : 733 - 739
[7] 57-NORMAJUSCULAMIDE-C, A MINOR CYCLIC DEPSIPEPTIDE ISOLATED FROM LYNGBYA-MAJUSCULA
MYNDERSE, JS
HUNT, AH
MOORE, RE
[J]. JOURNAL OF NATURAL PRODUCTS, 1988, 51 (06): : 1299 - 1301
[8] PETTIT GR, 1989, HETEROCYCLES, V28, P553

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