title: Toward L-homo-DNA: stereoselective de novo synthesis of β-L-erythro-hexopyranosyl nucleosides.
abstract: A novel route to 2',3'-dideoxy-β-l-erythro-hexopyranosyl nucleosides equipped with a 1'-(N(6)-benzoyladenin-9-yl) or a 1'-(thymin-1-yl) moiety has been developed. Synthesis of the enantiopure sugar moiety was carried out by a de novo approach based on a domino reaction as the key step. N-Glycosidation was explored via either nucleobase-transfer mechanism (B = T) or in situ anomerization (B = A or T), affording target nucleosides with high overall stereoselectivity.
authors.affiliation: Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cinthia 4, I-80126 Napoli, Italy. dandalonzo@unina.it
authors.forename: Daniele
authors.initials: D
authors.lastname: D'Alonzo
authors.forename: Annalisa
authors.initials: A
authors.lastname: Guaragna
authors.forename: Arthur
authors.initials: A
authors.lastname: Van Aerschot
authors.forename: Piet
authors.initials: P
authors.lastname: Herdewijn
authors.forename: Giovanni
authors.initials: G
authors.lastname: Palumbo
mesh_terms: D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009705:Nucleosides; D004247:DNA