ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS AND N-BENZOYL-3-PHENYLISOSERINES VIA THE STAUDINGER REACTION

被引：56

作者：

GEORG, GI

MASHAVA, PM

AKGUN, E

MILSTEAD, MW

机构：

[1] Department of Medicinal Chemistry University of Kansas, Lawrence

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)79708-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of benzaldimine 5 derived from 2,3,4,6-tetra-O-acetyl-beta-D-galactoseamine with acid chloride 6 yields cis beta-lactam 7 as a single diastereoisomer. Hydrolysis of beta-lactam 7 followed by N-benzoylation provides access toward N-benzoyl-(2S,3R)-3-phenylisoserine 9. N-Benzoyl-3-phenylisoserines are important building blocks for the semi-synthesis of the anti-cancer agent taxol.

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页码：3151 / 3154

页数：4

相关论文

共 19 条

[1] ASYMMETRIC-SYNTHESIS OF 1,3,4-TRISUBSTITUTED AND 3,4-DISUBSTITUTED 2-AZETIDINONES - STRATEGY BASED ON USE OF D-GLUCOSAMINE AS A CHIRAL AUXILIARY IN THE STAUDINGER REACTION [J].

BARTON, DHR ;

GATEAUOLESKER, A ;

ANAYAMATEOS, J ;

CLEOPHAX, J ;

GERO, SD ;

CHIARONI, A ;

RICHE, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3211-3212

[2] AN ASYMMETRIC-SYNTHESIS OF A 3-HYDROXY-BETA-LACTAM BY KETENE-IMINE CYCLOADDITION - UTILIZATION OF CHIRAL KETENES FROM CARBOHYDRATES [J].

BORER, BC ;

BALOGH, DW .

TETRAHEDRON LETTERS, 1991, 32 (08) :1039-1040

[3]

BOSE AK, 1990, 199TH NAT M AM CHEM

[4] CHIRAL CONTROL OF THE STAUDINGER REACTION [J].

COOPER, RDG ;

DAUGHERTY, BW ;

BOYD, DB .

PURE AND APPLIED CHEMISTRY, 1987, 59 (03) :485-492

[5] AN EFFICIENT, ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN [J].

DENIS, JN ;

GREENE, AE ;

SERRA, AA ;

LUCHE, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (01) :46-50

[6] AN IMPROVED SYNTHESIS OF THE TAXOL SIDE-CHAIN AND OF RP-56976 [J].

DENIS, JN ;

CORREA, A ;

GREENE, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1957-1959

[7] A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL [J].

DENIS, JN ;

GREENE, AE ;

GUENARD, D ;

GUERITTEVOEGELEIN, F ;

MANGATAL, L ;

POTIER, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5917-5919

[8] ASYMMETRIC-SYNTHESIS OF (1'R,3R,4R)-4-ACETOXY-3-(1'-((TERT-BUTYLDIMETHYLSILYL)OXY)ETHYL)-2-AZETIDINONE AND OTHER 3-(1'-HYDROXYETHYL)-2-AZETIDINONES FROM (S)-(+)-ETHYL 3-HYDROXYBUTANOATE - FORMAL TOTAL SYNTHESIS OF (+)-THIENAMYCIN [J].

GEORG, GI ;

KANT, J ;

GILL, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1129-1135

[9]

GEORG GI, UNPUB

[10]

HOLTON RA, COMMUNICATION