Efficient Syntheses of Clofarabine and Gemcitabine From 2-Deoxyribonolactone

Abstract

The development of a new methodology to achieve electrophilic fluorination of triisopropylsilyl-protected 2-deoxyribonolactone has been employed to synthesize clofarabine and gemcitabine with improved synthetic efficiency versus prior synthetic methods. These studies highlight the versatility of this new methodology to obtain medically relevant 2′-fluoronucleosides.

Keywords:

• Diastereoselective
• electrophilic fluorination
• 2-deoxyribonolactone

Notes

^a From acyl-protected ribofuranose.

^b From silyl-protected 2-deoxyribonolactone.

^a From isopropylidene glyceraldehyde.

^b From silyl-protected 2-deoxyribonolactone.