144364-03-4Relevant articles and documents
Synthesis of N-alkenylpurines by rearrangements of the corresponding N-allyl isomers: Scopes and limitations
Kania, Jindrich,Gundersen, Lise-Lotte
, p. 2008 - 2019 (2013)
N-9- and N-7-alkenylpurines have been synthesized by rearrangement of the corresponding N-allyl derivatives, often in good yields and with high stereoselectivity. Base promoted and transition metal mediated rearrangements have been studied. Simple allylpurines were easily rearranged with catalytic amounts of RuClH(CO)(PPh3)3. The efficiency of base promoted rearrangement was highly dependent on the detailed structure of the starting material, but this reaction often occurred with surprisingly high Z-selectivity. N-Alkenylpurines have been synthesized, often in good yields, from the corresponding more readily available N-allyl isomers by a double bond migration. The scope and limitation of the rearrangement in the presence of various bases or transition metal complexes have been studied.
Regiochemistry and Stereochemistry in Pd(0)-Catalyzed Allylic Alkylation of Nucleoside Bases
Gundersen, Lise-Lotte,Benneche, Tore,Rise, Frode,Gogoll, Adolf,Undheim, Kjell
, p. 761 - 771 (2007/10/02)
Allylic alkylation of amino- and hydroxy-azaheterocycles, in particular nucleoside bases, has been effected using Pd(0)-catalysis.A method has been developed for the preparation of carbocyclic nucleoside analogs such as the antiviral agent Carbovir.The synthesis of an appropriately substituted cyclopentenyl acetate for this reaction is described.Carbocyclic nucleosides of thymine at N-1, of adenine at N-9 and guanine at N-9 are described.Regiochemistry and stereochemistry of the products and intermediates have been determined by NMR studies.The (trimethylsilyl)ethyl group has been found to be an excellent protecting group for the 6-OH group in guanine, and it is readily removed by fluoride ions.
