Synthesis of 4-oxo- and 4-anti-formyl-8,10,12,13 -tetraoxapentacyclo[5.5.1.02,6.03,11.05,9]tridecanes

Article abstract of DOI:10.1016/S0040-4020(97)10228-9

The synthesis of 4-oxo- and 4-anti-formyl-8,10,12,13 -tetraoxapentacyclo[5.5.1.0^2,6.0^3,11.0^5,9]tridecanes has been accomplished. Ozonolysis of compounds 10a,b and 12a-c in dichloromethane at -78°C followed by reduction with dimethyl sulfide gave the title compounds, 4-oxo-tetraoxa-cages 11a,b and 14a-c, in moderate yields. Ozonolysis of the endo-syn isomers 15a,b and 18a,b under the same reaction conditions gave 4-anti-formyl-tetraoxa-cages 17a,b and 20a,b, respectively.