Stereocontrolled syntheses of deoxyribonucleosides via photoinduced electron-transfer deoxygenation of benzoyl-protected ribo- and arabinonucleosides.
The stereocontrolled, de novo syntheses of beta-2'-deoxy-, alpha-2'-deoxy-, beta-3'-deoxy-, and beta-2', 3'-dideoxyribonucleosides are described. Strategically protected ribose, arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrüggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl- or 3-(trifluoromethyl)benzoyl derivative. This deoxygenation is accomplished via a photoinduced electron-transfer (PET) mechanism using carbazole derivatives as the photosensitizer. The syntheses of the desired deoxynucleoside generally proceed in three steps from a common, readily available precursor.
Wang
Z
Z
Department of Chemistry, Box 1822, Station B, Vanderbilt University, Nashville, Tennessee 37235, USA.
Prudhomme
D R
DR
Buck
J R
JR
Park
M
M
Rizzo
C J
CJ
D001087:Arabinonucleosides / Q000737:chemistry*; D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D012263:Ribonucleosides / Q000737:chemistry*; D013237:Stereoisomerism
D001087:Arabinonucleosides; D003853:Deoxyribonucleosides; D012263:Ribonucleosides