100101-50-6Relevant articles and documents
Chiral syntheses of 6′-β-fluoroaristeromycin, 6′-β-fluoro-5′-noraristeromycin and aristeromycin
Yin, Xue-Qiang,Schneller, Stewart W.
, p. 7535 - 7538 (2007/10/03)
Carbocyclic nucleosides substituted at the C-6′ position are receiving increasing attention. Chiral synthetic accessibility to the biologically promising 6′-β-fluoroaristeromycin is lacking. Its preparation and that of the 5′-nor analogue are described. A
Enzyme-Catalysed Hydrolyses of Some Meso-Diesters
Cotterill, Ian C.,Cox, Philip B.,Drake, Alex F.,Grand, Darren M. Le,Hutchinson, Edward J.,et al.
, p. 3071 - 3076 (2007/10/02)
The diester 7 is hydrolysed, using porcine pancreatic lipase as catalyst, to give the monoester 8.The latter compound has been converted into the known azido alcohol 9 and into the purine derivative 10.Pig liver esterase (ple) catalysed hydrolysis of the diester 11 gave the acid 13 not the enantiomer 12 as previously reported.The structure of 13 was determined by its conversion into the compound ent-10.The diesters 17 and 18 are converted into the mono-esters 20 and 21 respectively using ple: hydrolysis of the diester 16 yields a mono-acid of high optical purity.The structure of this mono-acid is believed to be that shown in formula 19.
A Novel and Stereospecific Synthesis of (+/-)- and (-)-Aristeromycin
Madhavan, G. V. Bindu,Martin, John C.
, p. 1287 - 1293 (2007/10/02)
A new, efficient synthetic route to (+/-)- and (-)-aristeromycin (1) has been developed which has as its key feature the cycloaddition of singlet oxygen to 5--1,3-cyclopentadiene (8) followed by in situ reduction to give ene diol 10.This reaction has been optimized and scaled-up to give 197 g (60percent) of partially purified 10.The key intermediate azide 15 was prepared from the partially purified 10 in 56percent yield by a three-step sequence of epoxidation to give 13, reaction with NaN3, and acetonation.Azide 15 was converted by standard chemistry via adenine intermediate 22 to (+/-)-aristeromycin (1) in 31percent overall yield.Intermediate 22 was also prepared in 25percent yield by a novel and shorter sequence which involved the reaction of epoxide 13 with the sodium salt of adenine and then acetonation.Alternatively, azide 15 was resolved by conversion to its naproxen ester 26, and the (-)-isomer of 15 was converted to the known amino triol 31, thus constituting a formal synthesis of (-)-aristeromycin.
