title: Synthesis of EFdA via a diastereoselective aldol reaction of a protected 3-keto furanose.
abstract: An efficient enantioselective total synthesis of EFdA, a remarkably potent anti-HIV nucleoside analogue with various favorable pharmacological profiles, has been achieved in 37% overall yield from diacetone-D-glucose by a 14-step sequence that features a highly diastereoselective installation of the tetrasubstituted stereogenic center at the C4' position, direct oxidative cleavage of an acetonide-protected diol derivative to an aldehyde, and one-pot 2'-deoxygenation of a ribonucleoside intermediate.
authors: Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University , Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
authors: Kei
authors: K
authors: Fukuyama
authors: Hiroshi
authors: H
authors: Ohrui
authors: Shigefumi
authors: S
authors: Kuwahara
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry; D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000737:chemistry; D007661:Ketoses / Q000737:chemistry*; D015394:Molecular Structure; D012263:Ribonucleosides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D019380:Anti-HIV Agents; D003839:Deoxyadenosines; D007661:Ketoses; D012263:Ribonucleosides; C558823:islatravir