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Paper | Regular issue | Vol 60, No. 12, 2003, pp.2737-2742
Published online, 14th October, 2003
DOI: 10.3987/COM-03-9904
Preparation of 2’-3’-Epimino-carbocyclic Nucleosides Based on 2-Azabicyclo[2.2.1]hept-5-en-3-one

Minoru Ishikura,* Kota Matsumoto, Miyako Hasunuma, and Nobuya Katagiri

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan

Abstract

The thermal reaction of N-substituted 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) (1) with tosyl azide, which allowed the stereoselective introduction of an aziridine moiety into ABH (1), led to the facile construction of 6-azabicyclo[3.1.0]hexane (3). Successful conversion of 3 to the hitherto unknown 2’,3’-epimino-carbocyclic nucleosides (8) could be attained through a series of steps.