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Asymmetric Synthesis of (-)-6'-β-Fluoro-aristeromycin via Stereoselective Electrophilic Fluorination
Gyudong Kim1, Ji-Seong Yoon1, Dnyandev B Jarhad1
1Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University , Seoul, 151-742, Korea.
Organic Letters
|October 14, 2017
Abstract:
(-)-6'-β-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'-β-fluoro-isoaristeromycin (2a). Computational analysis indicates that the fluorine atom controlled the regioselectivity of the purine base substitution.