Synthesis of 3,5,7-trioxapentacyclo[7.2.1.0(2,8).0(4,11).0(6,10)]dodecane. A novel diacetal trioxa-cage

Abstract

3,5,7-Trioxapentacyclo[7.2.1.0(2,8).0(4,11).0(6,10)] dodecane, the parent compound of novel diacetal trioxa-cages, was synthesized from maleic anhydride cyclopentadiene adduct 1 by a four-step sequence. Attempts for the synthesis of monoaza dioxa-cage 12 failed. Ozonolysis of compound 9 in CH2Cl2-EtOH (1:1) at -78 degrees C followed by reduction with Me(2)S gave 13 in 65% yield.