ORGANOIRON COMPLEXES IN ORGANIC-SYNTHESIS .3. APPROACH TO THE SYNTHESIS OF SPIROCYCLIC COMPOUNDS FROM TRICARBONYLDIENE-IRON COMPLEX INTERMEDIATES

被引:47
作者
PEARSON, AJ
机构
[1] University Chemical Laboratory, Cambridge CB2 1EW, Lensfield Road
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 05期
关键词
D O I
10.1039/p19790001255
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of methyl 8-methoxy-2-oxospiro[4.5]deca-6,8-diene-3-carboxylate (14) in eight steps from p-methoxycinnamic acid is described. The method involves cyclisation of the 1,1-disubstituted-cyclohexa-2,4-diene (2d) which is readily obtained from tricarbonyl[η-1-5-1-(3′-methoxycarbonylpropyl)- 4-methoxycyclohexa-2,4-dienylium]iron hexafluorophosphate (3b). A similar series of reactions starting from 4-(p-methoxyphenyl) butyric acid leads ultimately to methyl 3-methoxy-8-oxospiro[5.5]undeca-1,3-diene-9-carboxylate (16). In the course of investigating model systems the trichodermin intermediate (1c) has also been synthesised.
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页码:1255 / 1260
页数:6
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