METALATION OF PI-DEFICIENT HETEROCYCLES A FACILE SYNTHESIS OF CERPEGIN

被引:22
作者
GUILLIER, F [1 ]
NIVOLIERS, F [1 ]
BOURGUIGNON, J [1 ]
DUPAS, G [1 ]
MARSAIS, F [1 ]
GODARD, A [1 ]
QUEGUINER, G [1 ]
机构
[1] INSA,IRCOF LAB,CHIM ORGAN FINE & HETEROCYCL LAB,CNRS,BP08,F-76131 MONT ST AIGNAN,FRANCE
关键词
CERPEGIN; SYNTHESIS; METALATION;
D O I
10.1016/S0040-4039(00)60186-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of the naturally occuring cerpegin is described. Metalation of a pyridine derivative has been used in the key step.
引用
收藏
页码:7355 / 7356
页数:2
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