SYNTHESIS AND REARRANGEMENT OF DISPIRO-, DISPIRO- AND DISPIROUNDECANES - NEW ENTRIES TO PROPELLANES

Article abstract of DOI:10.1016/S0040-4020(01)85699-4

The dispiroketones 4-6 have been synthesized and rearranged by treatment with acids yielding the bicyclic enone 36 under kinetic control and the <3.3.3>propellane 37 under thermodynamic control.The corresponding alcohols 10-12 all yield the <3.3.3>propellane 41.The rearrangement of <7,7-D2>-12 to <8,8-D2>-41 proceeds stereospecifically and points to dispirane 42 as potential precursor of(+/-)modhephene 43.Likewise, dispiranes 44 and 46 are potential precursors of (+/-)-isocomene 45.