129082-21-9Relevant academic research and scientific papers
PHOTO-OXIDATIVE CLEAVAGE OF A FURAN-AZETIDINONE CARBON-CARBON BOND: A SYNTHESIS OF 4-ACETOXYAZETIDINONE
Lynch, Joseph E.,Laswell, William L.,Volante, Ralph P.,Reamer, Robert A.,Tschaen, David M.,Shinkai, Ichiro
, p. 1029 - 1037 (2007/10/02)
A stereoselective synthesis of the 4-acetoxyazetidinione (1) from methyl 3(R)-hydroxybutyrate is reported.The synthesis involved stereoselective preparation of a 4-(2-furanyl)azetidinone that was allowed to react with singlet oxygen.The resulting endoperoxide intermediates underwent direct rearrangement to an acyloxyazetidinone that on reaction with sodium acetate gave 1 in modest yield.An improved yield of 1 was obtained by treatment of the endoperoxides with hydrogen peroxide followed by acetic anhydride to give an α-alkoxy acylperoxide that underwent thermal rearrangement to 1.
