We report our discovery of a novel carbon-carbon bond cleaving reaction. In this process cyclic γ-silyloxy-β-hydroxy-α-diazoesters (e.g. 1; Scheme 1) undergo efficient rupture of the C_β-C_γ bond when treated with tin tetrachloride to provide tethered aldehyde ynoate products (e.g. 2; Scheme 1) in high yield. These tethered aldehyde ynoates participate in intramolecular azomethine ylide 1,3-dipolarcycloadditions to provide tricyclic 2,5-dihydropyrroles (e.g. 3; Scheme 1) in good yield. This process has been extended to a one pot ring fragmentation / intramolecular azomethine ylide 1,3-dipolarcycloaddition with modest conversions. The scope, efficiency and mechanistic hypothesis of these transformations will be discussed. Preliminary results of our efforts to apply this methodology in the total synthesis of Solanidine (e.g. 5; Scheme 1) from commercially available androstenolone (e.g. 4; Scheme 1), will also be discussed.