STEREOCONTROLLED SYNTHESIS OF N,O-DIMETHYL-GAMMA-AMINO-BETA-HYDROXY ACIDS - ANALOGS OF THE (R)-MEILE-PSI(CHOME)-GLY RESIDUE OF THE CYTOTOXIC MARINE PSEUDOPEPTIDE DOLASTATIN-10

被引：48

作者：

MAUGRAS, I ^{[1
]}

PONCET, J ^{[1
]}

JOUIN, P ^{[1
]}

机构：

[1] CCIPE,RUE CARDONILLE,F-34094 MONTPELLIER 2,FRANCE

来源：

TETRAHEDRON | 1990年 / 46卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(01)88373-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereocontrolled synthesis of the N,O-dimethylated-γ-amino-β-hydroxy acid (R)-MeVal-ψ(CHOMe)-Gly (3b) is reported; the key step is the formation of the nonmethylated allylic precursor with the anti configuration 20 by reduction of the keto analogue 16. © 1990.

引用

收藏

页码：2807 / 2816

页数：10

相关论文

共 24 条

[1]

BENKESER RA, 1971, SYNTH-INT J METHODS, P347

[2] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].

CARLSEN, PHJ ;

KATSUKI, T ;

MARTIN, VS ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938

[3] N-METHYLAMINO ACIDS IN PEPTIDE-SYNTHESIS .5. SYNTHESIS OF N-TERT-BUTYLOXYCARBONYL, N-METHYLAMINO ACIDS BY N-METHYLATION [J].

CHEUNG, ST ;

BENOITON, NL .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (05) :906-910

[4] ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - THE SYNTHESIS OF ALPHA'-AMINO-ALPHA, BETA-YNONES [J].

CUPPS, TL ;

BOUTIN, RH ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :3972-3979

[5]

DEGNAN BM, 1989, J MED CHEM, V35, P1349

[6] SYNTHESIS AND REDUCTION OF ALPHA-AMINO KETONES DERIVED FROM LEUCINE [J].

DUFOUR, MN ;

JOUIN, P ;

PONCET, J ;

PANTALONI, A ;

CASTRO, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1895-1899

[7]

FEHRENTZ JA, 1983, SYNTHESIS-STUTTGART, P676

[8]

Gilman H., 1929, J AM CHEM SOC, V51, P1576

[9]

HARRIS BD, 1988, J ORG CHEM, V53, P869

[10] SYNTHESIS OF THE CYCLODEPSIPEPTIDE NORDIDEMNIN-B, A CYTO-TOXIC MINOR PRODUCT ISOLATED FROM THE SEA TUNICATE TRIDIDEMNUM-CYANOPHORUM [J].

JOUIN, P ;

PONCET, J ;

DUFOUR, MN ;

PANTALONI, A ;

CASTRO, B .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :617-627