The Diels-Alder reaction has been employed to synthesise a hexaepoxyoctacosahydrocyclacene derivative 6 in a highly efficient manner from the syn-isomer 1 of 1,4:5,8-diepoxy-1,4,5,8-tetrahydroanthracene and 2,3,5,6-tetramethylene-7-oxabicyclo[2.2.1]heptane 2. Each time a new cyclohexene ring is formed in the macropolycyclisation process, which utilises two molar equivalents of both the bisdienophile 1 and the bisdiene 2, the cycloadditions are trebly diastereoselective. A sequence of reactions on compound 6 involving (i) deoxygenation, (ii) dehydration, and (iii) partial hydrogenation have led to the isolation and characterisation of the D6h symmetrical dodecahydrocyclacene derivative 10 containing six benzene rings. The synthetic strategy is new and the macropolycyclic compounds, which can be prepared according to this kind of molecular’LEGO’, are novel.
ASJC Scopus subject areas
- Chemical Engineering(all)