000221836 001__ 221836
000221836 005__ 20190317000540.0
000221836 0247_ $$2doi$$a10.1002/ijch.201500090
000221836 022__ $$a0021-2148
000221836 02470 $$2ISI$$a000379976000020
000221836 037__ $$aARTICLE
000221836 245__ $$aNucleoside Analogues: Synthesis from Strained Rings
000221836 260__ $$bWiley-V C H Verlag Gmbh$$c2016$$aWeinheim
000221836 269__ $$a2016
000221836 300__ $$a12
000221836 336__ $$aJournal Articles
000221836 520__ $$aNucleoside analogues are widely employed as bioactive compounds against cancer and viral infections. Consequently, it is important to develop efficient synthetic methods to access them with high efficiency and structural diversity. Herein, we present a full account of our work on the synthesis of nucleoside analogues via annulations of donor acceptor aminocyclopropanes and aminocyclobutanes. Thymine- and uracil-derived diester cyclopropanes were accessed from the corresponding nucleobases via vinylation and rhodium-catalyzed cyclopropanation, and were then used in (3+2) annulations with aldehydes, ketones and enol ethers. The obtained analogues could be transformed into important hydroxymethyl derivatives. Thymine and fluoro-uracil-derived diester cyclobutanes obtained from the nucleobases via vinylation and (2+2) cycloaddition could also be used in a (4+2) annulation with aldehydes. Finally, purine-derived diester cyclopropanes could be accessed using the condensation of nucleobases with chloromethyl ethylidene malonates, but annulation reactions with this class of substrates were not successful.
000221836 6531_ $$aannulation
000221836 6531_ $$acatalysis
000221836 6531_ $$acyclopropanes
000221836 6531_ $$anucleosides
000221836 6531_ $$asynthetic methods
000221836 700__ $$0246623$$g215126$$aRacine, Sophie
000221836 700__ $$aVuilleumier, Jeremy
000221836 700__ $$aWaser, Jerome$$g181574$$0243584
000221836 773__ $$j56$$tIsrael Journal Of Chemistry$$k6-7$$q566-577
000221836 8564_ $$uhttps://infoscience.epfl.ch/record/221836/files/IJC2016-566GreenAccess.pdf$$zn/a$$s5601696$$yn/a
000221836 909C0 $$xU11811$$0252236$$pLCSO
000221836 909CO $$ooai:infoscience.tind.io:221836$$qGLOBAL_SET$$pSB$$particle
000221836 917Z8 $$x181574
000221836 917Z8 $$x181574
000221836 937__ $$aEPFL-ARTICLE-221836
000221836 973__ $$rREVIEWED$$sPUBLISHED$$aEPFL
000221836 980__ $$aARTICLE