De novo synthesis of 4'-ethoxy nucleoside analogues.
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.
Hegedus
Louis S
LS
Department of Chemistry, Colorado State University, Fort Collins 80523, USA. hegedus@lamar.colostate.edu
Geisler
Lisa
L
Riches
Andrew G
AG
Salman
Sarri S
SS
Umbricht
Gisela
G
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D005663:Furans / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D009705:Nucleosides; C004511:butenolide; D015107:4-Butyrolactone