First synthesis of 2',3'-epimino-carbocyclic nucleosides.
The preparation of 2',3'-epimino-carbocyclic analogues of adenosine is reported. The reaction of p-tosyl azide with N-substituted 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) (1a) provided aziridine-fused ABH (2), which was converted to 2',3'-epimino-carbocyclic nucleosides (11).
Ishikura
Minoru
M
Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan. ishikura@hoku-iryo-u.ac.jp
Murakami
Atsushi
A
Katagiri
Nobuya
N
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D001386:Azides / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D009705:Nucleosides / Q000737:chemistry*
D001386:Azides; D007769:Lactams; D009705:Nucleosides; C062350:2-azabicyclo(2.2.1)hept-5-en-3-one; D000241:Adenosine