THE FIRST ENANTIOSELECTIVE SYNTHESIS OF THE CHEMOTACTIC FACTOR SIRENIN BY AN INTRAMOLECULAR [2+1] CYCLIZATION USING A NEW CHIRAL CATALYST

被引:124
作者
GANT, TG [1 ]
NOE, MC [1 ]
COREY, EJ [1 ]
机构
[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138
关键词
D O I
10.1016/0040-4039(95)01924-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, highly enantioselective synthesis of sirenin (1) (bioactive form) has been developed which depends on the intramolecular [2 + 1] cycloaddition reaction of diazo ester 5 to form bicyclic ester 6 (95:5 enantioselectivity) using a new and remarkably stable monomeric chiral Cu(I) complex (2) whose structure was proven by X-ray diffraction analysis.
引用
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页码:8745 / 8748
页数:4
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