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.

引用

页码：3151 / 3154

页数：4

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
BARTON, DHR
GATEAUOLESKER, A
ANAYAMATEOS, J
CLEOPHAX, J
GERO, SD
CHIARONI, A
RICHE, C
[J]. 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
BORER, BC
BALOGH, DW
[J]. TETRAHEDRON LETTERS, 1991, 32 (08) : 1039 - 1040
[3] BOSE AK, 1990, 199TH NAT M AM CHEM
[4] CHIRAL CONTROL OF THE STAUDINGER REACTION
COOPER, RDG
DAUGHERTY, BW
BOYD, DB
[J]. PURE AND APPLIED CHEMISTRY, 1987, 59 (03) : 485 - 492
[5] AN EFFICIENT, ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN
DENIS, JN
GREENE, AE
SERRA, AA
LUCHE, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (01) : 46 - 50
[6] AN IMPROVED SYNTHESIS OF THE TAXOL SIDE-CHAIN AND OF RP-56976
DENIS, JN
CORREA, A
GREENE, AE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1957 - 1959
[7] A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL
DENIS, JN
GREENE, AE
GUENARD, D
GUERITTEVOEGELEIN, F
MANGATAL, L
POTIER, P
[J]. 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
GEORG, GI
KANT, J
GILL, HS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) : 1129 - 1135
[9] GEORG GI, UNPUB
[10] HOLTON RA, COMMUNICATION

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