A SIMPLE AND HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF A 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE BY DEALLYLOXYCARBONYLATION USING PALLADIUM COMPLEXES

被引:26
作者
MURAYAMA, T [1 ]
YOSHIDA, A [1 ]
KOBAYASHI, T [1 ]
MIURA, T [1 ]
机构
[1] TAKASAGO INT CORP,CENT RES LAB,HIRATSUKA 254,KANAGAWA,JAPAN
关键词
D O I
10.1016/0040-4039(94)85196-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Simple, highly diastereoselective synthesis of the key 1 beta-methylcarbapenem intermediate 1 has been accomplished via a palladium catalyzed deallyloxycarbonylation of diallyl malonate derivative 4a which was readily prepared from (3S,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidimone 2 in two steps.
引用
收藏
页码:2271 / 2274
页数:4
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[38]   SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF FR21818, A NEW, POTENT 1-BETA-METHYLCARBAPENEM [J].
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CHIBA, T ;
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MORINAGA, C ;
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TAWARA, S ;
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