DPPA-PROMOTED DECARBONYLATION OF A N-CBZ-(D,L)-PIPECOLINIC ACID-DERIVATIVE - AN EASY ENTRY TO [4.5]SPIROLACTAMS AND [4.5]SPIROLACTONES - TOTAL SYNTHESIS OF (+/-)-DELTA-CONICEINE

被引:20
作者
MARTINLOPEZ, MJ [1 ]
BERMEJOGONZALEZ, F [1 ]
机构
[1] UNIV SALAMANCA,FAC QUIM,DEPT QUIM ORGAN,E-37008 SALAMANCA,SPAIN
关键词
D O I
10.1016/S0040-4039(00)73161-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 6-benzyloxycarbonyl-1-oxa-6-azaspiro[4.5]decane-2-one 7a and 6-benzyloxycarbonyl-1,6-diazaspiro[4.5]decane-2-one 7b from (D,L)-pipecolinic acid is described. The extremely clean decarbonylation of the alpha-substituted amino acid 9d promoted by diphenylphosphorazidate (DPPA) is the key step of our strategy. The total synthesis of (+/-)-delta-coniceine (16) from the enamine ester 10a has been successfully achieved.
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页码:4235 / 4238
页数:4
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