Efficient syntheses of clofarabine and gemcitabine from 2-deoxyribonolactone.
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.
Cen
Yana
Y
Department of Pharmacology, Weill Medical College of Cornell University, New York, NY 10065, USA.
Sauve
Anthony A
AA
D000227:Adenine Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001087:Arabinonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D000077866:Clofarabine; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013400:Sugar Acids / Q000737:chemistry*; D000093542:Gemcitabine
D000227:Adenine Nucleotides; D000970:Antineoplastic Agents; D001087:Arabinonucleosides; D013400:Sugar Acids; D003841:Deoxycytidine; C056405:2,4,5-trihydroxypentanoic acid gamma-lactone; D000077866:Clofarabine; D000093542:Gemcitabine