Regioselective Synthesis of 5-Endo,6-Endo-Dihydroxy-7-Oxabicyclo[2.2.1]Heptan-2-One with Differential Protection of the Diol Group
The introduction of two hydroxy groups with differential protection at the endo positions of C(5) and C(6) of the ''naked sugars of the first generation'' has been achieved by seleno-Pummerer rearrangement of 5-endo-hydroxy-6-exa-phenylseleno-7-oxabicyclo[2.2.1]heptan-2-one derivatives followed by deselenation with Bu(3)SnH.
Keywords: Seleno-pummerer rearrangement ; naked sugars ; 5-endo ; 6-endo-dihydroxy-7-oxabicyclo[2.2.1]heptan-2-one ; 5-endo ; 6-exo-dihydroxy-7-oxabicyclo[2.2.1]heptan-2-one ; Derivatives naked sugars ; diels-alder reactions ; 7-oxabicyclo<2.2.1>hept-5-en-2-yl derivatives ; stereoselective ; synthesis ; electrophilic additions ; acetate ; acids ; furan ; route
Univ lausanne,bch dorigny,chim sect,ch-1015 lausanne,switzerland.
Record created on 2005-11-09, modified on 2016-08-08