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“Trans-Positioning” Carbons Within Strained Caged Bicyclic(S): Rom/Rcm (Ring-Opening/Ring-Closing) Metathesis And Dieckmann/Retro-Dieckmann Condensation Routes To A Cis-Decalin Infrastructure, Stefan Malone Cooper Jr

LSU Doctoral Dissertations

This dissertation describes methodology work involving a “Trans-Positioning” motif engaging strategically positioned carbons within a strained bi-carbocyclic core and on a tethered free-dangling hydrocarbon chain ultimately for skeletal rearrangement. Trans-alkenylation and trans-acylation processes are devised for investigation with bicyclo[2.2.2]octyl and bicyclo[2.2.1]heptyl strained cores. Recent advances in olefin metathesis led to an independent proposal of the now applicable, RRM (Ring-Rearranging Metathesis) for trans-alkenylation purposes. A resourceful Dieckmann/retro-Dieckmann sequence is devised for trans-acylation motives. Finally, this dissertation includes atypical diastereoselective reductions and additions which were serendipitously found with trigonal carbon atoms appended to our pertinent strained systems while in pursuit of our …