title: Selective Lewis acid catalyzed assembly of phosphonomethyl ethers: three-step synthesis of tenofovir.
abstract: Described herein is a novel Lewis acid catalyzed rearrangement-coupling of oxygen heterocycles and bis(diethylamino)chlorophosphine that provides direct formation of the phosphonomethyl ether functionality found in several important antiretroviral agents. A wide range of dioxolanes and 1,3-dioxanes may be employed, furnishing the desired products in good yield. The utility of this method is demonstrated in a novel synthesis of tenofovir, an antiretroviral drug used in the treatment of HIV/AIDS and hepatitis B.
authors: Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
authors: Charles E
authors: CE
authors: Ocampo
authors: Doris
authors: D
authors: Lee
authors: Timothy F
authors: TF
authors: Jamison
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D004146:Dioxanes / Q000737:chemistry*; D004148:Dioxolanes / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*; D000068698:Tenofovir
chemical_list: D004146:Dioxanes; D004148:Dioxolanes; D004987:Ethers; D005021:Ethylamines; D058116:Lewis Acids; D063065:Organophosphonates; D010720:Phosphines; C000600939:bis(diethylamino)chlorophosphine; D000068698:Tenofovir; D000225:Adenine