A linchpin carbacyclization approach for the synthesis of carbanucleosides.
A convenient synthesis of carbanucleosides, with both enantiomers equally accessible, is reported. The key step is a tandem linchpin cyclization process to give access to substituted carbafuranose derivatives having the correct relative stereochemistry for subsequent nucleobase introduction with inversion of configuration at C1. This was illustrated by the synthesis of 2',3'-dideoxycarbathymidine via a convergent nucleobase introduction and of 2',3'-dideoxy-6'-hydroxycarbauridine via a linear nucleobase introduction. Both methods relied on Mitsunobu chemistry, and the first example of the Mukaiyama modification of the Mitsunobu reaction involving nucleobases as nucleophiles is reported.
Leung
Leo M H
LM
School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK.
Gibson
Vicky
V
Linclau
Bruno
B
D019380:Anti-HIV Agents / Q000494:pharmacology; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D005663:Furans / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D005663:Furans; D009711:Nucleotides