Diastereo- and regioselective synthesis of diquinanes and related systems from tricyclo[3.3.0.02,4]octanes by chemical electron transfer (CET)

Article abstract of DOI:10.1055/s-1995-4072

A new synthetic methodology for diquinanes by one-electron oxidation of tricyclo[3.3.0.0^2,4]octanes and subsequent stereocontrolled rearrangement is provided. The latter compounds are conveniently accessible through acid-catalyzed isopyrazole cycloaddition, followed by hydrogenation and photoextrusion of molecular nitrogen. The oxidative rearrangement of the tricyclooctanes proceeds catalytically and cleanly to afford regio- and diastereoselectively the corresponding diquinanes.