Our Tactics in Ring Enlargement - Construction of Medium and Large Ring Compounds

Abstract

This Account presents our tactics in the synthesis of medium and large ring compounds. First the application of an oxanorbornadiene → oxepine ring enlargement to the synthesis of a [6]paracyclophane, of hydroazulenes, and bridged furanosides is described. Transformations of the Diels-Alder adduct of cyclooctyne and furan led to the synthesis of (-)-muricatacin and guided our way into Fragrance Chemistry. Finally, the stereoselective synthesis of macrocyclic odorants by way of ring enlargement of cycloalkanones with chiral building blocks is highlighted.