title: De novo synthesis of 4'-ethoxy nucleoside analogues.
abstract: Butenolides 5a and 13 were used as optically active templates in the de novo synthesis of 4'-disubstituted nucleoside analogues. The butenolides were reduced and acylated in situ to give acetates 10 and 14. Vorbrüggen coupling gave the protected nucleoside analogues 11 and 15. Reduction of 11 gave 4'-ethoxy-2',3'-dideoxythymidine (6) and deprotection of 15 gave 4'-ethoxy-2',3'-dideoxydidehydrothymidine (7). The cis-dihydroxylation of a variety of butenolides occurred with the major product formed from oxidation of the beta-face.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins 80523, USA. hegedus@lamar.colostate.edu
authors.forename: Louis S
authors.initials: LS
authors.lastname: Hegedus
authors.forename: Lisa
authors.initials: L
authors.lastname: Geisler
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Riches
authors.forename: Sarri S
authors.initials: SS
authors.lastname: Salman
authors.forename: Gisela
authors.initials: G
authors.lastname: Umbricht
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives; D005663:Furans / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D009705:Nucleosides; C004511:butenolide; D015107:4-Butyrolactone