Palladium-Catalyzed Synthesis of Carcinogenic Polycyclic Aromatic Hydrocarbon Epoxide-Nucleoside Adducts:  The First Amination of a Chloro Nucleoside1

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 r...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 5; no. 1; pp. 39 - 42
Main Authors Lakshman, Mahesh K., Gunda, Padmaja
Format Journal Article
LanguageEnglish
Published American Chemical Society 09.01.2003
Online AccessGet full text

Cover

More Information
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027084w