Palladium-catalyzed synthesis of carcinogenic polycyclic aromatic hydrocarbon epoxide-nucleoside adducts: The first amination of a chloro nucleoside

被引:30
作者
Lakshman, MK [1 ]
Gunda, P [1 ]
机构
[1] CUNY City Coll, Dept Chem, New York, NY 10031 USA
关键词
D O I
10.1021/ol027084w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pd-catalyzed coupling of the axially constrained, less reactive benzo[a]pyrene bay-region amino benzoates, derived from the tetrahydro and diol epoxides, with C-6 and C-2 halopurine deoxynucleosides offers an efficient approach to the synthesis of the corresponding nucleoside-epoxide adducts. Also reported are the first examples involving the coupling of a 6-chloropurine deoxynucleoside with these amines, a reaction that is difficult by direct halide displacement. Certain mechanistic aspects of this metal-catalyzed C-N bond formation are also discussed.
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页码:39 / 42
页数:4
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