Synthesis of 9-oxa-noradamantane derivative, an aesthetically pleasing ‘oxa-basket’

A simple protocol for the synthesis of an aesthetically pleasing ‘oxa-basket’ (5-methoxy-2,8,13-trioxapentacyclo[7.2.1.1.5,120.4,1106,10]tridecane-3,7-dione), possessing 9-oxa-noradamantane core, is described. The readily available diquinane based dichloro bis-γ-lactone precursor upon treatment with MeSO3H furnished dichloro ‘oxa-basket’ which was dechlorinated using TBTH/AIBN to obtain the title compound. The key role of the chlorines was demonstrated by replacement with hydrogen or allyl substituents which redirects the cascade to simple hydrolysis products.