A new synthetic approach to the clinically useful, anti-HIV-active nucleoside, 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (β-FddA). Introduction of a 2′-β-fluoro substituent via inversion of a readily obtainable 2′-α-fluoro isomer

Add time:08/08/2019    Source:sciencedirect.com

A convenient route to the anti-HIV active compound, 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (1, β-FddA) started with the facile introduction of fluorine at C2′ from the α-side of protected 9-(β-D-arabinofuranosyl)adenine (ara-A). Inversion of the stereochemistry at C2′ was accomplished via a stable vinyl intermediate (6), which underwent stereoselective reduction of the double bond to give the desired 2′-F-threo isomer with the opposite β-fluoro stereochemistry.

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