Asymmetric Synthesis of (?)-6'-Beta-Fluoro-aristeromycin via stereoselective electrophilic fluorination

Kim, G.; Yoon, J-S.; Jarhad, D.B.; Shin, Y.S.; Majik, M.S.; Mulamoottil, V.A.; Qu, X.H.S.; Park, J.; Baik, M-H.; Jeong, L.S.

Asymmetric Synthesis of (?)-6'-Beta-Fluoro-aristeromycin via stereoselective electrophilic fluorination

Kim, G.; Yoon, J-S.; Jarhad, D.B.; Shin, Y.S.; Majik, M.S.; Mulamoottil, V.A.; Qu, X.H.S.; Park, J.; Baik, M-H.; Jeong, L.S.

Source : Organic Letters. 19; 2017; 5732-5735.

URI: http://dx.doi.org/10.1021/acs.orglett.7b02470
http://irgu.unigoa.ac.in/drs/handle/unigoa/5324

Date: 2017

Document Type: Journal article

Abstract:

(?)-6'-Beta-Fluoro-aristeromycin (2), a potent inhibitor of S-adenosylhomocysteine (AdoHcy) hydrolase, has been synthesized via stereoselective electrophilic fluorination followed by a purine base build-up approach. Interestingly, purine base condensation using a cyclic sulfate resulted in a synthesis of (+)-5'-Beta-fluoro-isoaristeromycin (2a). Computational analysis indicates that the fluorine atom controlled the regioselectivity of the purine base substitution.

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