98601-03-7Relevant articles and documents
Purines. LVII. Regioselective alkylation of N6,9-disubstituted 8- oxoadenines: Syntheses of the sea anemone purine caissarone and some positional isomers and analogues
Saito,Mori,Chikazawa,Kanai,Fujii
, p. 1746 - 1752 (2007/10/02)
The first total synthesis of caissarone hydrochloride (1), a constituent of the sea anemone Bunodosoma caissarum, has been accomplished via a two- step route starting from N6,9-dimethyl-8-oxoadenine (3), which is obtainable from 9-methyladenine (5) through a four-step route. The key step in the synthesis is the regioselective methylation of 3 at N(3), which has been designed on the basis of a methylation study of N6-benzyl-9-methyl-8- oxoadenine (11). Some positional isomers (19, 24, and 31) and analogues (8, 26, and 32) of 1 have also been synthesized. A 1H-NMR spectroscopic study has suggested that the free base (23) of caissarone is capable of forming a hetero-base pair (such as 41) with 2',3',5'-tri-O-acetylguanosine (40) in Me2SO-d6.
Purines. XLIII. A total synthesis of the marine sponge base 6-imino-1,9-dimethyl-8-oxopurine
Fujii,Saito,Mori
, p. 2146 - 2150 (2007/10/02)
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