SYNTHESIS OF ALPHA,BETA-UNSATURATED SPIROLACTAMS BY INTRAMOLECULAR CYCLIZATION OF ENDOCYCLIC N-ACYLIMINIUM IONS

被引:11
|
作者
MARTIN, MJ [1 ]
BERMEJO, F [1 ]
机构
[1] UNIV SALAMANCA,FAC QUIM,DEPT QUIM ORGAN,E-37008 SALAMANCA,SPAIN
关键词
D O I
10.1016/0040-4039(95)01568-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of (+/-)-6-benzyl-3-methyl-3-en-1,6-diazaspiro-[4.5]decane-2,7-dione (18), the spiro moiety of (+/-)-pandamarine has been achieved try oxidative cyclization of the (Z) and (E) isomers of 5-(N-benzyl-4-carboxamido-butylidene)-3-methyl-3-en-pyrrolin-2-one (15a) and(15b). The stereoselectivity exhibited in the intramolecular cyclization by both butylidene precursors has also been discussed.
引用
收藏
页码:7705 / 7708
页数:4
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