SYNTHESIS OF APENTACYCLO[5.5.1.0(2,6).0(3,11).0(5,9)]TRIDECANES AND APENTACYCLO[5.5.1.0(2,6).0(3,11).0(5,9)]TRIDECANES

The synthesis of 4-oxo- and apentacyclo[5.5.1.0(2,6).0(3,11).0(5,9)]tr idecanes has been accomplished. Ozonolysis of compounds 10a,b and 12a- c in dichloromethane at -78 degrees C followed by reduction with dimet hyl sulfide gave the title compounds, 4-oxo-tetraoxa-cages 11a,b and 1 4a-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. (C) 1997 Published by Elsevier Sc ience Ltd.