Stereoselective synthesis of (2R,3S,4S,5R)-trans-3,4-dihydroxy-5-(4-fluorophenoxymethyl)-2-(1-N-hydroxyureidyl-3-butyn-4-yl)tetrahydrofuran and (2R,3S,4S,5R)-trans-5-ethynyl-2-(4-fluorophenoxymethyl)-3,4-O-isopropylidene tetrahydrofuran from mannose diacetonide

Mitsunobu and Related Reactions: Advances and Applications

“…Similar furan ring construction (using n -Bu 3 P−TMAD) in the synthesis of C -aryl nucleotides has been reported by Wengel and co-workers . Other examples of intramolecular etherification leading to a five-membered ring involve (i) 3′-β- C -branched anhydromannitol nucleosides, (ii) epoxyphenylmorphans, (iii) flavone C -glycosides, (iv) [(2 R ,3 R )-3-aminotetrahydrofuran-2-yl]imidazole, (v) (α- d -xylofuranosyl)imidazoles, (vi) indole/thiazole-appended C -nucleosides, (vii) isonucleosides, (viii) furan-3,4-dicarboxylic acid, (ix) cycloalkenobenzofurans, (x) 3-aryl-2,3-dihydrobenzofurans, (xi) fluorescent 3-aminobiphenyl- C -nucleosides, (xii) 2-amino-5-(2-deoxy-β- d -ribofuranosyl)pyridine, (xiii) β-ribofuranosides, (xiv) pharmaceutically interesting chiral tetrahydrofurans, (xv) 4(5)-( β - d -ribofuranosyl)imidazole, (xvi) 8-oxa-3-azabicyclo[3.2.l]octane-6,7-diol, and (xvii) 3′-β- C -branched anhydrohexitol nucleosides . The structural drawings corresponding to these references are given in the Supporting Information (Table S5).…”