DIASTEREOSELECTIVE ZIRCONOCENE-PROMOTED BICYCLIZATION-CARBONYLATION OF ALLYLICALLY METHYL-SUBSTITUTED ENYNES - SYNTHESIS OF (+)-IRIDOMYRMECIN

被引:61
作者
AGNEL, G [1 ]
OWCZARCZYK, Z [1 ]
NEGISHI, E [1 ]
机构
[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907
关键词
D O I
10.1016/S0040-4039(00)91669-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allylically methyl-substituted 1,6-heptenynes, such as 3-methyl-1,6-octenyne, can be diastereoselectively converted to the corresponding bicyclic ketones, such as (5R,6S)-2,6-dimethylbicyclo[3.3.0]oct-1-en-3-one readily convertible to (+)-iridomyrmecin, the observed diastereomeric excesses of the bicyclization reaction being > 90%.
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页码:1543 / 1546
页数:4
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