Synthesis of β-hydroxywybutines, the most probable alternatives for the hypermodified base of rat liver phenylalanine transfer ribonucleic acid

Deoxygenation of the 1,2-glycol (±)-5 was achieved at the position adjacent to the heterocycle through the cyclic carbonate (±)-14, providing the monohydroxy compound 6. This new method of regioselective deoxygenation was employed for the first synthesis of β-hydroxywybutines [[R-(R ∗ ,S ∗ )]- and [S-(R ∗ ,R ∗ )]-2] : oxidation of the methyl butenoate 7 with osmium tetroxide, followed by deoxygenation through the cyclic carbonates (19 and 20), afforded the two diastereomers of 2.